Phenyl sulfonamides

ABSTRACT

N-phenylsulfonyl-N&#39;-pyrimidinyl- and -triazinylureas of the general formula ##STR1## and the salts thereof with amines, alkali metal or alkaline earth metal bases or with quaternary ammonium bases, have good pre- and postemergence selective herbicidal and growth regulating properties. In the above formula 
     A is a C 1  -C 6  alkyl radical which is substituted by C 1  -C 4  alkoxy, C 1  -C 4  alkylthio, C 1  -C 4  alkylsulfinyl, C 1  -C 4  alkylsulfonyl, C 1  -C 4  haloalkoxy, C 1  -C 4  haloalkylthio, C 1  -C 4  haloalkylsulfinyl or C 1  -C 4  haloalkylsulfonyl, or a C 2  -C 6  alkenyl radical which is unsubstituted or substituted by the above substituents, or is a C 2  -C 6  haloalkenyl radical, 
     E is the methine group or nitrogen, 
     X is oxygen, sulfur, a sulfinyl or sulfonyl bridge, 
     Z is oxygen or sulfur, 
     m is 1 or 2, 
     R 1  is hydrogen, halogen, C 1  -C 5  alkyl, C 2  -C 5  alkenyl or a radical --Y--R 5 , 
     R 2  is hydrogen, halogen, C 1  -C 5  alkyl, C 2  -C 5  alkenyl, C 1  -C 4  haloalkyl, or a radical --Y--R 5 , --COOR 6 , --NO 2  or --CO--NR 7  --R 8 , 
     R 3  and R 4 , each independently of the other, are hydrogen, C 1  -C 4  alkyl, C 1  -C 4  alkoxy, C 1  -C 4  alkylthio, C 1  -C 4  haloalkyl, halogen or alkoxyalkyl of at most 4 carbon atoms, 
     R 5  and R 6 , each independently of the other, are C 1  -C 5  alkyl, C 2  -C 5  alkenyl or C 2  -C 6  alkynyl, 
     R 7  and R 8 , each independently of the other, are hydrogen, C 1  -C 5  alkyl, C 2  -C 5  alkenyl or C 2  -C 6  alkynyl, and 
     Y is oxygen, sulfur, a sulfinyl or sulfonyl bridge.

This is a division of application Ser. No. 417,743, filed on Sept. 13, 1982, now U.S. Pat. No. 4,510,325, issued Apr. 9, 1985, which is a division of application Ser. No. 282,847 filed on July 13, 1981, now abandoned.

The present invention relates to novel N-phenylsulfonyl-N'-pyrimidinyl- and triazinylureas having herbicidal and plant growth-regulating properties, to the production thereof, to compositions containing them, and to the use thereof for controlling weeds, in particular selectively, in crops of useful plants, or for regulating and inhibiting plant growth. The invention also relates to novel phenylsulfonamides prepared as intermediates.

The N-phenylsulfonyl-N'-pyrimidinyl- and -triazinylureas of this invention have the general formula I ##STR2## wherein A is a C₁ -C₆ alkyl radical which is substituted by C₁ -C₄ alkoxy, C₁ -C₄ alkylthio, C₁ -C₄ alkylsulfinyl, C₁ -C₄ alkylsulfonyl, C₁ -C₄ haloalkoxy, C₁ -C₄ haloalkylthio, C₁ -C₄ haloalkylsulfinyl, or C₁ -C₄ haloalkylsulfonyl, or a C₂ -C₆ alkenyl radical which is unsubstituted or substituted by the above substituents, or is a C₂ -C₆ haloalkenyl radical,

E is the methine group or nitrogen,

X is oxygen, sulfur, a sulfinyl or sulfonyl bridge,

Z is oxygen or sulfur,

m is 1 or 2,

R₁ is hydrogen, halogen, C₁ -C₅ alkyl, C₂ -C₅ alkenyl or a radical --Y--R₅,

R₂ is hydrogen, halogen, C₁ -C₅ alkyl, C₂ -C₅ alkenyl, C₁ -C₄ haloalkyl, or a radical --Y--R₅, --COOR₆, --NO₂ or --CO--NR₇ --R₈,

R₃ and R₄, each independently of the other, are hydrogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ alkylthio, C₁ -C₄ haloalkyl, halogen or alkoxyalkyl of at most 4 carbon atoms,

R₅ and R₆, each independently of the other, are C₁ -C₅ alkyl, C₂ -C₅ alkenyl or C₂ -C₆ alkynyl,

R₇ and R₈, each independently of the other, are hydrogen, C₁ -C₅ alkyl, C₂ -C₅ alkenyl or C₂ -C₆ alkynyl, and

Y is oxygen, sulfur, a sulfinyl or sulfonyl bridge, and salts of these compounds.

Herbicidally active ureas, triazines and pyrimidines are generally known in the art. Arylsulfamoyl-heterocyclylaminocarbamoyl compounds with herbicidal and plant growth-regulating action have recently been described, for example in European patent publication Nos. 1514 and 1515, U.S. Pat. No. 4,127,405, German Offenlegungsschrift No. 2 715 786 or French patent specification No. 1 468 747.

In the above definitions, alkyl denotes straight-chain or branched alkyl, e.g. methyl, ethyl, n-propyl, isopropyl, the four isomers of butyl, n-amyl, isoamyl, 2-amyl, 3-amyl, n-hexyl or isohexyl, with straight-chain alkyl being preferred.

Alkoxy denotes methoxy, ethoxy, n-propyloxy, isopropyloxy and the four butyloxy isomers, and is, in particular, methoxy or ethoxy.

Alkylthio is e.g. methylthio, ethylthio, n-propylthio, isopropylthio and n-butylthio, with methylthio and ethylthio being preferred.

Examples of alkenyl radicals are vinyl, allyl, isopropenyl, 1-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-isobutenyl, 2-isobutenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl and 4-pentenyl, with vinyl, allyl and 4-pentenyl being preferred.

Alkylsulfinyl is e.g. methylsufinyl, ethylsulfinyl, n-propylsulfinyl and n-butylsulfinyl, with methylsulfinyl and ethylsulfinyl being preferred.

Alkylsulfonyl is e.g. methylsulfonyl, ethylsulfonyl, n-propylsulfonyl and n-butylsulfonyl, with methylsulfonyl and ethylsulfonyl being preferred.

Halogen in the definitions of R₁ to R₄ and in haloalkoxy, haloalkylsulfinyl, haloalkylsulfonyl, haloalkylthio and haloalkenyl is fluorine, chlorine and bromine, with fluorine and chlorine being preferred.

The invention also comprises the salts which the compounds of formula I are able to form with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases.

Preferred salt-forming alkali metal and alkaline earth metal hydroxides are the hydroxides of lithium, sodium, potassium, magnesium or calcium, most preferably of sodium or potassium.

Examples of suitable salt-forming amines are primary, secondary and tertiary aliphatic and aromatic amines such as methylamine, ethylamine, propylamine, isopropylamine, the four isomeric butylamines, dimethylamine, diethylamine, diethanolamine, dipropylamine, diisopropylamine, di-n-butylamine, pyrrolidine, piperidine, morpholine, trimethylamine, triethylamine, tripropylamine, quinuclidine, pyridine, quinoline and isoquinoline. Preferred amines are ethylamine, propylamine, diethylamine or triethylamine, with isopropylamine and diethanolamine being most preferred.

Examples of quaternary ammonium bases are, in general, the cations of haloammonium salts, e.g. the tetramethylammonium cation, the trimethylbenzylammonium cation, the triethylbenzylammonium cation, the tetraethylammonium cation, the trimethylethylammonium cation, and also the ammonium cation.

Preferred compounds of the formula I are those in which

(a) Z is oxygen and

(b) R₃ and R₄ together contain not more than 4 carbon atoms.

Group (a) can be divided into two further subgroups which consist of compounds in which

(aa) m is 1, and

(ab) m is 2.

Preferred compounds in group (aa) are those in which the radical --X--A is in the 2- or 3-position to the sulfonyl radical. Among these preferred compounds further preference attaches to those compounds in which the radical --X--A is in the 2-position.

A preferred group of compounds in group (ab) comprises those compounds in which both radicals --X--A are in the 2 and 5-position to the sulfonyl group.

A further preference in connection with compounds of the above subgroups (aa) and (ab) consists in the feature that the radicals R₃ and R₄ together contain at most 4 carbon atoms. Accordingly, particularly preferred groups of compounds of formula I are the groups

(aab) in which only one radical --X--A is in the 2-position to the sulfonyl radical, Z is oxygen and R₃ and R₄ together contain not more than 4 carbon atoms, and

(abb) in which two radicals --X--A are in the 2- and 5-position to the sulfonyl radical, Z is oxygen and R₃ and R₄ together contain not more than 4 carbon atoms.

Preferred compounds of the group (aab) are those in which R₁ is hydrogen and R₂ is in the 5- or 6-position to the sulfonyl group. Among these preferred compounds, preference attaches in turn to those compound in which R₂ is hydrogen, halogen, C₁ -C₄ alkoxy, nitro or COOR₆.

Further preferred compounds within this last mentioned group are those in which R₂ is hydrogen, fluorine, nitro or C₁ -C₄ alkoxy, and each of R₃ and R₄ is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ alkylthio, halogen or alkoxyalkyl, whilst R₃ and R₄ together contain at most 4 carbon atoms.

Among these compounds, preferred compounds are in turn those in which R₂ is hydrogen and each of R₃ and R₄ is C₁ -C₄ alkyl, C₁ -C₄ alkoxy, methylthio, halogen or alkoxyalkyl.

Further preferred compounds within this last mentioned group are those in which X is oxygen or sulfur. Of these compounds, the most preferred are in turn those in which A is C₂ -C₈ alkoxyalkyl, C_(2-C) ₄ haloalkenyl or C₂ -C₆ alkenyl.

Three preferred subgroups of compounds belonging to this last group are those in which

(α) A is C₂ -C₈ alkoxyalkyl and each of R₃ and R₄ is methyl, ethyl, chlorine or methoxy,

(β) A is C₂ -C₆ alkenyl and each of R₃ and R₄ is methyl, ethyl, chlorine or methoxy, and

(γ) A is vinyl substituted by 1 to 3 halogen atoms and each of R₃ and R₄ is methyl, ethyl, chlorine or methoxy.

Of the compounds of formula I in which Z is sulfur, those compounds are preferred in which X is oxygen or sulfur, R₃ and R₄, each independently of the other, are C₁ -C₃ alkyl, C₁ -C₃ alkoxy or C₁ -C₃ alkylthio, containing together at most 4 carbon atoms, and A is --CH₂ --CH═CH₂, --CH₂ --CH═CH--CH₃, --CH₂ --CH(CH₃)═CH₂, methoxyethyl, methoxymethyl or --CCl═CHCl, and the radical --X--A is in the 2-position and m is 1.

A preferred individual compound is N-(2-allyloxyphenylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea.

The process for obtaining the compounds of formula I is carried out in an inert organic solvent.

In a first process, the compounds of the formula I are obtained by reacting a phenylsulfonamide of the formula II ##STR3## wherein A, R₁, R₂, X and m are as defined for formula I, in the presence of a base, with a N-pyrimidinyl- or N-triazinylcarbamate of the formula III ##STR4## wherein E, R₃, R₄ and Z are as defined for formula I.

In a second process, compounds of formula I are obtained by reacting a phenylsulfonylisocyanate or phenylsulfonylisothiocyanate of the formula IV ##STR5## wherein A, R₁, R₂, m, X and Z are as defined for formula I, optionally in the presence of a base, with an amine of the formula V ##STR6## wherein E, R₃ and R₄ are as defined for formula I.

In a further process, the compounds of formula I are obtained by reacting a sulfonamide of the formula II above, optionally in the presence of a base, with an isocyanate or isothiocyanate of the formula VI ##STR7## wherein E, R₃, R₄ and Z are as defined for formula I.

Finally, the compounds of formula I can also be obtained by reacting a N-phenylsulfonylcarbamate of the formula VII ##STR8## wherein A, R₁, R₂, m and X are as defined for formula I, with an amine of the formula V above.

If desired, the ureas of formula I can be converted into salts with amines, alkali metal or alkaline earth metal hydroxides or quaternary ammonium bases. This conversion is carried out e.g. by reacting the compounds of formula I with the equimolar amount of a base and removing the solvent by evaporation.

Some of the starting materials of the formulae II, IV and VII are novel and can be prepared by the following methods.

The novel sulfonamides of formula II used as intermediates are obtained from the corresponding anilines by diazotisation and replacement of the diazo group, with sulfur dioxide, in the presence of a catalyst such as copper(I) chloride, in hydrochloric acid or acetic acid, and reacting the resultant phenylsulfonyl chloride with ammonium hydroxide solution.

The compounds of formula II can also be obtained by O- or S-alkylation or O- or S-alkenylation of hydroxy- or thiophenylsulfonamides with the corresponding halides or sulfuric acid esters, or by reaction of ortho-halophenylsulfonamides with metal alcoholates or mercaptides and, if desired, by oxidation thereof e.g. with periodates or peracids to give the corresponding sulfoxides and sulfones.

Ortho-hydroxyphenylsulfonamides or substituted ortho-hydroxyphenylsulfonamides of the formula VIII ##STR9## wherein R₁ and R₂ are as defined for formula I and X' is oxygen or sulfur, as starting materials of specific sulfonamides of the formula II, are novel, with the exception of ortho-hydroxyphenylsulfonamide. They can be obtained by ether cleavage of corresponding C₁ -C₄ alkoxyphenylsulfonamides, e.g. with boron trihalides [such reactions are described in U.S. Pat. No. 3,904,680 and in J. Am. Chem. Soc, 64, 1128 (1942)] or by hydrogenolysis of the corresponding benzylphenylsulfonamides, as described in J. Chem. Soc. 1958, 2903.

The alkoxyphenylsulfonamides can, in turn, be obtained from the corresponding alkoxyanilides, as already mentioned, or by chlorosulfonylation of alkoxybenzenes and reaction of the resultant phenylsulfonyl chlorides with ammonium hydroxide solution. Such reactions are known from from J. Am. Chem. Soc. 62, 603 (1940).

The compounds of formulae II and VIII employed as intermediates are novel, or some are novel, and have been specially developed for the synthesis of compounds of formula I. These intermediates constitute a further object of the invention.

The phenylsulfonylisocyanates of the formula IV can be obtained by reacting the sulfonamides of the formula II with phosgene, in the presence of butylisocyanate in a chlorinated hydrocarbon as solvent, at reflux temperature. Similar reactions are described in "Newer Methods of Preparative Organic Chemistry", Vol. VI, 223-241, Academic Press, New York and London.

The isothiocyanates of the formula IV are obtained by treating the sulfonamides of formula II with carbon disulfide and potassium hydroxide and by subsequent reaction of the dipotassium salt with phosgene. Such processes are described in Arch. Pharm. 299, 174 (1966).

The N-phenylsulfonylcarbamates of the formula VII are obtained by reacting the sulfonamides of the formula II with diphenyl carbonate in the presence of a base. Similar processes are described in Japanese patent specification No. 61 169.

The starting materials of the formulae III, V and VI are known or they can be prepared by known methods.

Isocyanates of the formula VI can be prepared by reacting amines of the formula V with oxalyl chloride in a chlorinated hydrocarbon as solvent. Amines of the formula V are known and some are commercially available, or they can be prepared by known methods, q.v. "The Chemistry of Heterocyclic Compounds", Vol. XIV, Interscience Publishers, New York, London.

It is expedient to carry out the reactions for obtaining compounds of formula I in aprotic, inert organic solvents such as methylene chloride, tetrahydrofurane, acetonitrile, dioxane or toluene.

The reaction temperatures are preferably in the range from -20° and +120° C. The reactions are normally slightly exothermic and can be carried out at room temperature. To shorten the reaction time or also to initiate the reaction it is expedient to heat the reaction mixture briefly to boiling point. The reaction times can also be shortened by addition of a few drops of a base or isocyanate as catalyst.

The final products can be isolated by concentrating the reaction mixture and/or removing the solvent by evaporation, and by recrystallisation or by triturating the solid residue in solvents in which it is poorly soluble, such as ether, aromatic hydrocarbons or chlorinated hydrocarbons.

The compounds of formula I are stable compounds, and no protective measures are required for handling them.

The compounds of formula I have pronounced plant growth-regulating, especially plant growth-inhibiting, properties. The growth of both monocots and dicots is inhibited. Thus, for example, the compounds of formula I selectively inhibit the growth of leguminosae which are frequently planted as cover crops in tropical regions, so that, while soil erosion between cultivated plants is prevented, the cover crops cannot compete with the cultivated plants.

Further, the compounds of formula I are suitable for preventing stored potatoes from seeding. During winter storage, potatoes often develop sprouts which result in shrinkage, weight loss, and rot.

When the compounds of formula I are applied in higher rates of application, all tested plants are so damaged in their development that they wither. When used in lower rates of application, the compounds of formula I have good selective growth-inhibiting and selective herbicidal properties which make them most suitable for use in crops of useful plants, especially in cereals, cotton, soybeans, maize and rice. In some cases damage is also caused to weeds which have up to now have only been controlled with total herbicides.

The mode of action of these compounds is unusual. Many are translocatable, i.e. they are absorbed by the plant and transported to other parts of it where they then deploy their action. The unusual feature of the compounds is that they do not only take the path through the vascular bundle in the ligneous part from the roots to the leaves, but can also be translocated through the sieve tubes in the bast part of the leaves back into the roots. Thus, for example, it is possible to damage perennial weeds to the very roots by surface treatment. Compared with other herbicides and growth regulators, the novel compounds of the formula I are effective even when used in very low rates of application.

The invention also relates to herbicidal and plant growth-regulating compositions which contain a novel compound of the formula I, and also to methods of controlling weeds pre- and postemergence and of inhibiting the growth of monocots and dicots, especially grasses, tropical cover crops and tobacco plant suckers.

The compounds of the formula I are used in unmodified form or preferably together with the adjuvants conventionally employed in the art of formulation, and are therefore formulated in known manner to emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations in e.g. polymer substances. The methods of application, such as spraying, atomising, dusting, scattering or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances, just like the nature of the compositions.

The formulations, i.e. the compositions or preparations containing the compound (active ingredient) of the formula I and, where appropriate, a solid or liquid adjuvant, are prepared in known manner, e.g. by homogeneously mixing and/or grinding the active ingredients with extenders, e.g. solvents, solid carriers and, where appropriate, surface-active compounds (surfactants).

Suitable solvents are: aromatic hydrocarbons, preferably the fractions containing 8 to 12 carbon atoms, e.g. xylene mixtures or substituted naphthalenes, phthalates such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and glycols and their ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monomethyl or monoethyl ether, ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethyl formamide, as well as epoxidised vegetable oils such as epoxidised coconut oil or soybean oil; or water.

The solid carriers used e.g. for dusts and dispersible powders are normally natural mineral fillers such as calcite, talcum, kaolin, montmorillonite or attapulgite. In order to improve the physical properties it is also possible to add highly dispersed silicic acid or highly dispersed absorbent polymers. Suitable granulated adsorptive carriers are porous types, for example pumice, broken brick, sepiolite or bentonite; and suitable nonsorbent carriers are materials such as calcite or sand. In addition, a great number of pregranulated materials of inorganic or organic nature can be used, e.g. especially dolomite or pulverised plant residues.

Depending on the nature of the compound of formula I to be formulated, suitable surface-active compounds are nonionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties. The term "surfactants" will also be understood as comprising mixtures of surfactants.

Suitable anionic surfactants can be both water-soluble soaps and water-soluble synthetic surface-active compounds.

Suitable soaps are the alkali, alkaline earth or unsubstituted or substituted ammonium salts of higher fatty acids (C₁₀ -C₂₂), e.g. the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which can be obtained e.g. from coconut oil or tallow oil. Mention may also be made of fatty acid methyltaurin salts.

More frequently, however, so-called synthetic surfactants are used, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.

The fatty sulfonates or sulfates are usually in the form of alkali, alkaline earth or unsubstituted or substituted ammonium salts and contain a C₈ -C₂₂ alkyl radical which also includes the alkyl moiety of acyl radicals, e.g. the sodium or calcium salt of lignosulfonic acid, of dodecylsulfate or of a mixture of fatty alcohol sulfates obtained from natural fatty acids. These compounds also comprise the salts of sulfuric acid esters and sulfonic acids of fatty alcohol/ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and one fatty acid radical containing 8 to 22 carbon atoms. Examples of alkylarylsulfonates are the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or of a naphthalenesulfonic acid/formaldehyde condensation product. Also suitable are corresponding phosphates, e.g. salts of the phosphoric acid ester of an adduct of p-nonylphenol with 4 to 14 moles of ethylene oxide.

Non-ionic surfactants are preferably polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, or saturated or unsaturated fatty acids and alkylphenols, said derivatives containing 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moiety and 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols.

Further suitable non-ionic surfactants are the water-soluble adducts of polyethylene oxide with polypropylene glycol, ethylenediaminepolypropylene glycol and alkylpolypropylene glycol containing 1 to 10 carbon atoms in the alkyl chain, which adducts contain 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. These compounds usually contain 1 to 5 ethylene glycol units per propylene glycol unit.

Representative examples of non-ionic surfactants are nonylphenol-polyethoxyethanols, castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol. Fatty acid esters of polyoxyethylene sorbitan and polyoxyethylene sorbitan trioleate are also suitable non-ionic surfactants.

Cationic surfactants are preferably quaternary ammonium salts which contain, as N-substituent, at least one polyglycol ether or C₈ -C₂₂ alkyl radical and, as further substituents, lower unsubstituted or halogenated alkyl, benzyl or lower hydroxyalkyl radicals. The salts are preferably in the form of halides, methylsulfates or ethylsulfates, e.g. stearyltrimethylammonium chloride or benzyldi(2-chloroethyl)ethylammonium bromide.

The surfactants customarily employed in the art of formulation are described e.g. in the following publications: "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ringwodd, N.J., 1979; Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co. Inc., New York, 1964.

The pesticidal formulations usually contain 0.1 to 95%, preferably 0.1 to 80%, of a compound of the formula I, 1 to 99.9% of a solid or liquid adjuvant, and 0 to 25%, preferably 0.1 to 25%, of a surfactant.

Preferred formulations are composed in particular of the following constituents (%=percentage by weight):

SOLUTIONS

active ingredient: 1 to 30%, preferably 5 to 20%

solvent: 99 to 0%, preferably 95 to 0%

surfactants: 1 to 99%, preferably 0 to 95%

EMULSIFIABLE CONCENTRATES

active ingredient: 1 to 20%, preferably 5 to 10%

surfactant: 5 to 30%, preferably 10 to 20%

liquid carrier: 50 to 94%, preferably 70 to 85%

DUSTS

active ingredient: 0.1 to 10%, preferably 0.1 to 1%

solid carrier: 99.9 to 90%, preferably 99.9 to 99%

SUSPENSION CONCENTRATES

active ingredient: 5 to 75%, preferably 10 to 50%

water: 94 to 25%, preferably 90 to 30%

surfactant: 1 to 40%, preferably 2 to 30%

WETTABLE POWDERS

active ingredient: 0.5 to 90%, preferably 1 to 80%

surfactant: 0.5 to 20%, preferably 1 to 15%

solid carrier: 5 to 95%, preferably 15 to 90%

GRANULATES

active ingredient: 0.5 to 30%, preferably 3 to 15%

solid carrier: 99.5 to 70%, preferably 97 to 85%.

Whereas commercial products will be preferably formulated as concentrates, the end user will normally employ dilute formulations. The formulations can be diluted to a concentration as low as 0.001%. The rates of application are normally 0.01 to 10 kg a.i./ha, preferably 0.025 to 5 kg a.i./ha.

The compositions can also contain further ingredients such as stabilisers, antifoams, viscosity regulators, binders, adhesives, as well as fertilisers or other active compounds, in order to attain special effects.

PREPARATORY EXAMPLES Example 1 2-Hydroxyphenylsulfonamide

22.2 ml of boron tribromide are added dropwise, under nitrogen and at room temperature, over 15 minutes to a suspension of 39 g of 2-methoxyphenylsulfonamide in 210 ml of dry methylene chloride. The reaction mixture is then stirred for 1 hour at room temperature. After the mixture has been cooled to 0° C., 200 ml of methanol are added over 15 minutes and the clear solution is concentrated. The oily residue is taken up in ethyl acetate and the solution is washed twice with water, dried over sodium sulfate, and evaporated to dryness. The residue is triturated with petroleum ether, affording 25.1 g of 2-hydroxyphenylsulfonamide with a melting point of 136°-138° C.

The hydroxyphenylsulfonamides of the formula VIII listed in the following Table 1 are obtained in analogous manner:

                  TABLE 1                                                          ______________________________________                                          ##STR10##                                                                                          Position of Physical data                                 R.sub.1    R.sub.2   OH          (°C.)                                  ______________________________________                                          ##STR11## H         2           m.p. 90-91°                            2-CH.sub.3 H         5                                                         2-Cl       H         5                                                         5-F        H         2           m.p. 141-142°                          5-Br       H         2           m.p. 169-70°                           5-NO.sub.2 H         2           m.p. 180-185°                          3-CH.sub.3 H         2           m.p. 133-134°                          2-CH.sub.3 H         3                                                         3-Cl       H         2                                                         6-CH.sub.3 H         2                                                         3-OCH.sub.3                                                                               H         2                                                         2-OCH.sub.3                                                                               H         3                                                         3-CH.sub.3 5-t-C.sub.4 H.sub.9                                                                      2           m.p. 134-137°                          6-OCH.sub.3                                                                               H         2                                                         6-OH       H         2                                                         5-OCH.sub.3                                                                               H         2           m.p. 119-20°                           2-OCH.sub.3                                                                               H         5           m.p. 213-15°                           5-CH.sub.3 H         2           m.p. 155-156°                          6-Cl       H         2           m.p. 190-91°                           3-NO.sub.2 H         2                                                         3-COOCH.sub.3                                                                             H         2                                                         5-COOCH.sub.3                                                                             H         2           m.p. 171-172°                          5-Cl       H         2           m.p. 176-179°                          5-NO.sub.2 3-CF.sub.3                                                                               2                                                         5-NO.sub.2 3-Cl      2                                                         5-CF.sub.3 3-NO.sub.2                                                                               2                                                         5-CH.sub.3 3-CH.sub.3                                                                               2                                                         5-Cl       3-NO.sub.2                                                                               2                                                         5-Cl       3-Cl      2           m.p. 156-158°                          5-Br       3-OCH.sub.3                                                                              2                                                         5-Br       2-OCH.sub.3                                                                              3           m.p. 194-197°                          3-OCH.sub.3                                                                               5-COOCH.sub.3                                                                            2                                                         2-OCH.sub.3                                                                               5-COOCH.sub.3                                                                            3                                                         5-CH.sub.3 3-Br      2                                                         5-Br       3-NO.sub.2                                                                               2                                                         5-Br       3-COOCH.sub.3                                                                            2                                                         5-COOCH.sub.3                                                                             3-NO.sub.2                                                                               2                                                         5-Cl       3-Br      2           m.p. 247-249°                          3-NH.sub.2 H         2                                                         5-NH.sub.2 H         2                                                         5-COOC.sub.3 H.sub.7 (i)                                                                  3-NO.sub.2                                                                               2                                                         5-CON(CH.sub.3).sub.2                                                                     H         2                                                         6-NO.sub.2 H         2                                                         6-COOCH.sub.3                                                                             H         2                                                         ______________________________________                                    

Example 2 2-Allyloxyphenylsulfonamide

A mixture of 3.5 g of 2-hydroxyphenylsulfonamide, 5.5 g of potassium carbonate and 1.7 ml of allyl bromide in 100 ml of methyl ethyl ketone is stirred, under nitrogen, for 1 hour at reflux temperature. The reaction mixture is cooled to room temperature, filtered, and evaporated to dryness. One recrystallisation from ethyl acetate yields 3.27 g of 2-allyloxyphenylsulfonamide with a melting point of 104°-105° C.

Sulfonamides of the formula II which can be obtained in analogous manner are listed in Table 2.

                                      TABLE 2                                      __________________________________________________________________________      ##STR12##                                                                                                     Position                                                                             Physical                                 R.sub.1 R.sub.2                                                                              X  A              of XA data (°C.)                        __________________________________________________________________________     H       H     O  CClCHCl        2     m.p. 147-149°                     H       H     S  CClCHCl        2                                              H       H     SO CClCHCl        2                                              H       H     SO.sub.2                                                                          CClCHCl        2                                              H       H     O  CHCCl.sub.2    2                                              H       H     S  CHCCl.sub.2    2                                              H       H     SO CHCCl.sub.2    2                                              H       H     SO.sub.2                                                                          CHCCl.sub.2    2                                              H       H     O  CH.sub.2 CHCH.sub.2                                                                           2     m.p. 104-5°                       H       H     S  CH.sub.2 CHCH.sub.2                                                                           2                                              H       H     O                                                                                  ##STR13##     2     m.p. 104-105°                     H       H     S                                                                                  ##STR14##     2                                              H       H     O  (CH.sub.2).sub.2CHCH.sub.2                                                                    2                                              H       H     O  (CH.sub.2).sub.3CHCH.sub.2                                                                    2                                              H       H     O                                                                                  ##STR15##     2                                              H       H     S                                                                                  ##STR16##     2                                              H       H     O  CH.sub.2CHCHCH.sub.3                                                                          2     m.p. 113-114°                     H       H     S  CH.sub.2CHCHCH.sub.3                                                                          2                                              H       H     O                                                                                  ##STR17##     2                                              H       H     S                                                                                  ##STR18##     2                                              H       H     O  CH.sub.2OCH.sub.3                                                                             2     decomp.                                                                        from 121°                         H       H     O  CH.sub.2OC.sub.2 H.sub.5                                                                      2                                              H       H     O  CH.sub.2SCH.sub.3                                                                             2                                              H       H     O  CH.sub.2 CH.sub.2OCH.sub.3                                                                    2     m.p. 110-112°                     H       H     S  CH.sub.2 CH.sub.2OCH.sub.3                                                                    2                                              H       H     O  CH.sub.2 CH.sub.2OC.sub.2 H.sub. 5                                                            2                                              H       H     O  CH.sub.2 CH.sub.2SCH.sub.3                                                                    2                                              6-Cl    H     O  CH.sub.2 CHCH.sub.2                                                                           2     m.p. 127-128°                     6-Cl    H     O                                                                                  ##STR19##     2                                              6-Cl    H     O                                                                                  ##STR20##     2                                              6-Cl    H     O  CH.sub.2 OCH.sub.3                                                                            2                                              6-Cl    H     O  (CH.sub.2).sub.2 OCH.sub.3                                                                    2                                              6-Cl    H     O  CH.sub.2 SCH.sub.3                                                                            2                                              6-Cl    H     O  (CH.sub.2).sub.2 SCH.sub.3                                                                    2                                              6-Cl    H     O  CH.sub.2CHCHCH.sub.3                                                                          2                                              6-OCH.sub.3                                                                            H     O  CH.sub.2CHCH.sub.2                                                                            2                                              6-OCH.sub.3                                                                            H     O                                                                                  ##STR21##     2                                              6-OCH.sub.3                                                                            H     O  (CH.sub.2).sub.2OC.sub.2 H.sub.5                                                              2                                              6-OCH.sub.3                                                                            H     O                                                                                  ##STR22##     2                                              6-OCH.sub.3                                                                            H     O  (CH.sub.2).sub.2CHCH.sub.2                                                                    2                                              6-CH.sub.3                                                                             H     O  CH.sub.2CH CH.sub.2                                                                           2                                              6-CH.sub.3                                                                             H     O                                                                                  ##STR23##     2                                              6-CH.sub.3                                                                             H     O  (CH.sub.2).sub.2OCH.sub.3                                                                     2                                              6-CH.sub.3                                                                             H     O  CH.sub.2 SCH.sub.3                                                                            2                                              H       H     O  CH.sub.2 CH.sub.2OCH.sub.2 CHCH.sub.2                                                         2                                              6-NO.sub.2                                                                             H     O  CH.sub.2CHCH.sub.2                                                                            2                                              6-NO.sub.2                                                                             H     O  CH.sub.2CHCHCH.sub.3                                                                          2                                              6-NO.sub.2                                                                             H     O  CH.sub.2OCH.sub.3                                                                             2                                              6-NO.sub.2                                                                             H     O  CH.sub.2CH.sub.2OC.sub.2 H.sub.5                                                              2                                              6-NO.sub.2                                                                             H     O                                                                                  ##STR24##     2                                              6-COOCH.sub.3                                                                          H     O  CH.sub.2CHCH.sub.2                                                                            2                                              5-Cl    H     O  CH.sub.2CHCH.sub.2                                                                            2     m.p. 122°                         5-Cl    H     O                                                                                  ##STR25##     2                                              5-Br    H     O                                                                                  ##STR26##     2                                              5-Br    H     O  CH.sub.2CHCH.sub.2                                                                            2     m.p. 110-111°                     5-Br    H     O  CH.sub.2OCH.sub.3                                                                             2                                              5-F     H     O  CH.sub.2CHCH.sub.2                                                                            2     m.p. 113-114°                     5-F     H     O                                                                                  ##STR27##     2                                               ##STR28##                                                                             H     O                                                                                  ##STR29##     2                                               ##STR30##                                                                             H     O  CH.sub.2CHCH.sub.2                                                                            2     oil                                       ##STR31##                                                                             H     O  CH.sub.2 CH.sub.2 OCH.sub.3                                                                   2                                              5-CH.sub.3                                                                             H     O  CH.sub.2 CH.sub.2 OCH.sub.3                                                                   2                                              5-CH.sub.3                                                                             H     O  CH.sub.2CHCH.sub.2                                                                            2     m.p. 139-140°                     5-CH.sub.3                                                                             H     O  CH.sub.2CHCHCH.sub.3                                                                          2                                              5-NO.sub.2                                                                             H     O  CH.sub.2CHCHCH.sub.3                                                                          2                                              5-NO.sub.2                                                                             H     O  CH.sub.2SCH.sub.3                                                                             2                                              5-NO.sub.2                                                                             H     O  CH.sub.2 CHCH.sub.2                                                                           2     m.p. 138-141°                     5-OCH.sub.3                                                                            H     O  CH.sub.2 CHCH.sub.2                                                                           2     m.p. 88-89°                       5-OCH.sub.3                                                                            H     O                                                                                  ##STR32##     2                                              5-OCH.sub. 3                                                                           H     O  CH.sub.2 CHCHCH.sub.3                                                                         2                                              5-OCH.sub.3                                                                            H     O  CH.sub.2 OCH.sub.3                                                                            2                                              5-OCH.sub.3                                                                            H     O  CH.sub.2 CH.sub.2SCH.sub.3                                                                    2                                               ##STR33##                                                                             H     O  CH.sub.2CHCH.sub.2                                                                            2                                               ##STR34##                                                                             H     O                                                                                  ##STR35##     2                                              5-COOCH.sub.3                                                                          H     O  CH.sub.2CHCH.sub.2                                                                            2                                              5-COOCH.sub.3                                                                          H     O                                                                                  ##STR36##     2                                              5-COOCH.sub.3                                                                          H     O  CH.sub.2OC.sub.2 H.sub.5                                                                      2                                              5-NO.sub.2                                                                             3-CF.sub.3                                                                           O  CH.sub.2CHCH.sub.2                                                                            2                                              5-NO.sub.2                                                                             3-Cl  O  CH.sub.2CHCH.sub.2                                                                            2                                              5-NO.sub.2                                                                             3-Cl  O                                                                                  ##STR37##     2                                              5-CF.sub.3                                                                             3-NO.sub.2                                                                           O  CH.sub.2CHCH.sub.2                                                                            2                                              5-CH.sub.3                                                                             3-CH.sub.3                                                                           O  CH.sub.2CHCH.sub.2                                                                            2                                              5-CH.sub.3                                                                             3-CH.sub.3                                                                           O  CH.sub.2CHCHCH.sub.3                                                                          2                                              5-Cl    3-NO.sub.2                                                                           O  CH.sub.2CHCHCH.sub.3                                          5-Cl    3-Cl  O  CH.sub.2CHCH.sub.2                                                                            2     m.p. 161-162°                     5-Cl    3-Cl  O  CH.sub.2CH.sub.2OCH.sub.3                                                                     2                                              5-Cl    3-Cl  O  CH.sub.2OCH.sub.3                                                                             2                                              5-Br    3-OCH.sub.3                                                                          O  CH.sub.2CHCH.sub.2                                                                            2                                              5-Br    2-OCH.sub.3                                                                          O  CH.sub.2CHCH.sub.2                                                                            3     resin                                    3-OCH.sub.3                                                                            5-COOCH.sub.3                                                                        O  CH.sub.2CHCH.sub.2                                                                            2                                              2-OCH.sub.3                                                                            5-COOCH.sub.3                                                                        O                                                                                  ##STR38##     3                                              5-CH.sub.3                                                                             3-Br  O  CH.sub.2OCH.sub.3                                                                             2                                              5-Br    3-NO.sub.2                                                                           O  CH.sub.2 CHCH.sub.2                                                                           2                                              5-Cl    3-Br  O  CH.sub.2 CHCH.sub.2                                                                           2     m.p. 179°                         5-Cl    3-Br  O                                                                                  ##STR39##     2                                              5-Cl    3-Br  O  CH.sub.2CH.sub.2OCH.sub.3                                                                     3                                              H       H     SO CH.sub.2CHCH.sub.2                                                                            2                                              H       H     SO.sub.2                                                                          CH.sub.2CHCH.sub.2                                                                            2                                              H       H     SO CH.sub.2CHCHCH.sub.3                                                                          2                                              H       H     SO.sub.2                                                                          CH.sub.2CHCH CH.sub.3                                                                         2                                              H       H     O  CH.sub.2SOCH.sub.3                                                                            2                                              H       H     O  CH.sub.2SO.sub.2CH.sub.3                                                                      2                                              H       H     O  CH.sub.2CH.sub.2SOCH.sub.3                                                                    2                                              H       H     O  CH.sub.2CH.sub.2SO.sub.2CH.sub.3                                                              2                                              H       H     O                                                                                  ##STR40##     2                                              H       H     O                                                                                  ##STR41##     2                                              H       H     O                                                                                  ##STR42##     2                                              H       H     O                                                                                  ##STR43##     2                                              5-CH.sub.3                                                                             H     O                                                                                  ##STR44##     2                                              5-NO.sub.2                                                                             H     O                                                                                  ##STR45##     2                                              5-Br    H     O                                                                                  ##STR46##     2                                              5-Cl    H     O                                                                                  ##STR47##     2                                              5-CH(CH.sub.3).sub.2                                                                   H     O                                                                                  ##STR48##     2                                              3-CH.sub.3                                                                             H     O                                                                                  ##STR49##     2                                              6-CH.sub.3                                                                             H     O                                                                                  ##STR50##     2                                              6-OCH.sub.3                                                                            H     O                                                                                  ##STR51##     2                                              5-OCH.sub.3                                                                            H     O                                                                                  ##STR52##     2                                              6-Cl    H     O                                                                                  ##STR53##     2                                              3-NO.sub.2                                                                             H     O                                                                                  ##STR54##     2                                              3-CH.sub.3                                                                             H     O  CH.sub.2CHCH.sub.3                                                                            2     m.p. 114-116°                     3-NO.sub.2                                                                             H     O  CH.sub.2CHCH.sub.3                                                                            2                                              3-Cl    H     O  CH.sub.2CHCH.sub.3                                                                            2                                              3-Cl    H     O  CH.sub.2CHCHCH.sub.3                                                                          2                                              3-Cl    H     O                                                                                  ##STR55##     2                                              3-OCH.sub.3                                                                            H     O                                                                                  ##STR56##     2                                              3-OCH.sub.3                                                                            H     O  CH.sub.2CHCH.sub.2                                                                            2                                              2-OCH.sub.3                                                                            H     O  CH.sub.2CH CH.sub.2                                                                           5     m.p. 113-114°                     __________________________________________________________________________

Example 3 (a) N-(2-Allyloxyphenylsulfonyl)phenylcarbamate

2.76 g of 2-allyloxyphenylsulfonamide in 20 ml of dimethyl formamide are added dropwise, under nitrogen, over 5 minutes and at a maximum temperature of 20° C., to a suspension of 0.56 g of sodium hydride (55%) in 5 ml of absolute dimethyl formamide, and the suspension is stirred for about 10 minutes before the dropwise addition of 2.91 g of diphenyl carbonate in 20 ml of dimethyl formamide. The reaction mixture is stirred for a further 1/2 hour and then taken up in a mixture of 80 ml of ethyl acetate, 80 g of ice and 12.3 ml of 2N hydrochloric acid. The organic phase is washed twice with ice-water, dried over sodium sulfate and evaporated to dryness. Crystallisation from ether/petroleum ether (1:1) yields 3.5 g of N-(2-allyloxyphenylsulfonyl)phenylcarbamate with a melting point of 140°-141° C.

(b) N-(2-Allyloxyphenylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ure

A mixture of 3.33 g of N-(2-allyloxyphenylsulfonyl)phenylcarbamate and 1.4 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine in 30 ml of absolute dioxane is heated to reflux for 1/2 hour, then cooled to 20° C., filtered, evaporated to dryness, and the residue is crystallised from ether. Recrystallisation from ethyl acetate/petroleum ether (1:1) yields 2 g of N-(2-allyloxyphenylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea with a melting point of 146°-147° C.

The compounds of formula I listed in Table 3 are obtained in analogous manner:

                                      TABLE 3                                      __________________________________________________________________________      ##STR57##                                                                     No. A            R.sub.1 R.sub.3                                                                            R.sub.4                                                                            X  E  Physical data (°C.)              __________________________________________________________________________     1   CH.sub.2CHCH.sub.2                                                                          6-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          2   CH.sub.2CHCH.sub.2                                                                          6-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         3   CH.sub.2CHCH.sub.2                                                                          6-Cl    C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                          O  N                                          4   CH.sub.2CHCH.sub.2                                                                          6-Cl    OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                         5   CH.sub.2CHCH.sub.2                                                                          6-Cl    OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                               ##STR58##   6-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          7                                                                                   ##STR59##   6-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         8                                                                                   ##STR60##   6-Cl    C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                          O  N                                          9                                                                                   ##STR61##   6-Cl    OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          10                                                                                  ##STR62##   6-Cl    OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                         11  CH.sub.2CHCHCH.sub.3                                                                        6-Cl    OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                         12  CH.sub.2CHCHCH.sub.3                                                                        6-Cl    OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          13  CH.sub.2CHCHCH.sub.3                                                                        6-Cl    OCH.sub.3                                                                          CH.sub.3                                                                           O  N                                          14  CH.sub.2CHCHCH.sub.3                                                                        6-Cl    OCH.sub.3                                                                          CH.sub.3                                                                           O  CH                                         15                                                                                  ##STR63##   6-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          16                                                                                  ##STR64##   6-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         17  CH.sub.2 OCH.sub.3                                                                          6-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         18  CH.sub.2OCH.sub.3                                                                           6-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          19  CH.sub.2OCH.sub.3                                                                           6-Cl    C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                          O  N                                          20  (CH.sub.2).sub.2OCH.sub.3                                                                   6-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          21  (CH.sub.2).sub.2OCH.sub.3                                                                   6-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         22  CH.sub.2SCH.sub.2                                                                           6-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         23  CH.sub.2SCH.sub.2                                                                           6-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          24  (CH.sub.2).sub.2SCH.sub.2                                                                   6-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          25  (CH.sub.2).sub.2SCH.sub.2                                                                   6-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         26  CH.sub.2 CHCH.sub.2                                                                         6-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         27  CH.sub.2 CHCH.sub.2                                                                         6-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          28  CH.sub.2 CHCH.sub.2                                                                         6-OCH.sub.3                                                                            C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                          O  N                                          29  CH.sub.2 CHCH.sub.2                                                                         6-OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          30  CH.sub.2 CHCH.sub.2                                                                         6-OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                         31                                                                                  ##STR65##   6-OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                         32                                                                                  ##STR66##   6-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          33                                                                                  ##STR67##   6-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         34  (CH.sub.2).sub.2OC.sub.2 H.sub.5                                                            6-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         35  (CH.sub.2).sub.2OC.sub.2 H.sub.5                                                            6-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          36                                                                                  ##STR68##   6-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          37                                                                                  ##STR69##   6-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         38                                                                                  ##STR70##   6-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          39                                                                                  ##STR71##   6-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         40                                                                                  ##STR72##   6-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  CH m.p. 163-164°                    41                                                                                  ##STR73##   6-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  N  m.p. 142-145°                    42  CH.sub.2CHCH.sub.2                                                                          6-CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          43  CH.sub.2CHCH.sub.2                                                                          6-CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         44  CH.sub.2CHCH.sub.2                                                                          6-CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                         45  CH.sub.2CHCH.sub.2                                                                          6-CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          46                                                                                  ##STR74##   6-CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          47                                                                                  ##STR75##   6-CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         48                                                                                  ##STR76##   6-CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          49                                                                                  ##STR77##   6-CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                         50  CH.sub.2OCH.sub.3                                                                           6-CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                         51  CH.sub.2 OCH.sub.3                                                                          6-CH.sub.3                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           O  CH                                         52  CH.sub.2OCH.sub.3                                                                           6-CH.sub.3                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           O  N                                          53  (CH.sub.2).sub.2CHCH.sub.2                                                                  6-OCH.sub.3                                                                            OCH.sub.3                                                                          CH.sub.3                                                                           O  N                                          54  (CH.sub.2).sub.2CHCH.sub.2                                                                  6-OCH.sub.3                                                                            OCH.sub.3                                                                          CH.sub.3                                                                           O  CH                                         55  CH.sub.2SCH.sub.3                                                                           6-CH.sub.3                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           O  CH                                         56  CH.sub.2SCH.sub.3                                                                           6-CH.sub.3                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           O  N                                          57  CH.sub.2CHCH.sub.2                                                                          6-NO.sub.2                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          58  CH.sub.2CHCH.sub.2                                                                          6-NO.sub.2                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         59  CH.sub.2CHCH.sub.2                                                                          6-NO.sub.2                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                         60  CH.sub.2CHCH.sub.2                                                                          6-NO.sub.2                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          61  CH.sub.2CHCHCH.sub.3                                                                        6-NO.sub.2                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          62  CH.sub.2CHCHCH.sub.3                                                                        6-NO.sub.2                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                         63  CH.sub.2CHCHCH.sub.3                                                                        6-NO.sub.2                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           O  CH                                         64  CH.sub.2CHCH CH.sub.3                                                                       6-NO.sub.2                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           O  N                                          65  CH.sub.2OCH.sub.3                                                                           6-NO.sub.2                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           O  N                                          66  CH.sub.2OCH.sub.3                                                                           6-NO.sub.2                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           O  CH                                         67  CH.sub.2CH.sub.2OC.sub.2 H.sub.5                                                            6-NO.sub.2                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           O  CH                                         68  CH.sub.2CH.sub.2OC.sub.2 H.sub.5                                                            6-NO.sub.2                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           O  N                                          69                                                                                  ##STR78##   6-NO.sub.2                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           O  N                                          70                                                                                  ##STR79##   6-NO.sub.2                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           O  CH                                         71  CH.sub.2CHCH.sub.2                                                                          6-COOCH.sub.3                                                                          OCH.sub.3                                                                          CH.sub.3                                                                           O  CH                                         72  CH.sub.2CHCH.sub.2                                                                          6-COOCH.sub.3                                                                          OCH.sub.3                                                                          CH.sub.3                                                                           O  N                                          73  CH.sub.2CHCH.sub.2                                                                          6-COOCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          74  CH.sub.2CHCH.sub.2                                                                          6-COOCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                         75  CH.sub.2 CHCH.sub.2                                                                         5-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          76  CH.sub.2 CHCH.sub.2                                                                         5-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         77  CH.sub.2 CHCH.sub.2                                                                         5-Cl    OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          78  CH.sub.2 CHCH.sub.2                                                                         5-Cl    OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          79  CH.sub.2 CHCH.sub.2                                                                         5-Cl    C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                          O  N                                          80                                                                                  ##STR80##   5-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          81                                                                                  ##STR81##   5-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         82  CH.sub.2 CHCH.sub.2                                                                         5-Br    CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         83  CH.sub.2 CHCH.sub.2                                                                         5-Br    CH.sub.3                                                                           OCH.sub.3                                                                          O  N  m.p. 190-191°                    84  CH.sub.2 CHCH.sub.2                                                                         5-Br    C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           O  N                                          85                                                                                  ##STR82##   5-Br    CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          86                                                                                  ##STR83##   5-Br    OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          87                                                                                  ##STR84##   5-Br    CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         88  CH.sub.2OCH.sub.3                                                                           5-Br    CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         89  CH.sub.2OCH.sub.3                                                                           5-Br    CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          90  CH.sub.2CHCH.sub.2                                                                          5-F     CH.sub.3                                                                           OCH.sub.3                                                                          O  N  m.p. 159-161°                    91  CH.sub.2CHCH.sub.2                                                                          5-F     CH.sub.3                                                                           OCH.sub.3                                                                          O  CH m.p. 200-201°                    92  CH.sub.2CHCH.sub.2                                                                          5-F     OCH.sub.3                                                                          C.sub.2 H.sub.5                                                                    O  N                                          93  CH.sub.2CHCH.sub.2                                                                          5-F     OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH m.p. 162-164°                    94                                                                                  ##STR85##   5-F     CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          95                                                                                  ##STR86##   5-F     CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         96                                                                                  ##STR87##   5-F     CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         97                                                                                  ##STR88##   5-F     CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          98                                                                                  ##STR89##                                                                                   ##STR90##                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          99                                                                                  ##STR91##                                                                                   ##STR92##                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         100                                                                                 ##STR93##                                                                                   ##STR94##                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         101                                                                                 ##STR95##                                                                                   ##STR96##                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          102 CH.sub.2CHCH.sub.2                                                                           ##STR97##                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  N  m.p. 259-260°                    103 CH.sub.2CHCH.sub.2                                                                           ##STR98##                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  CH m.p. 139-140°                    104 CH.sub.2CHCH.sub.2                                                                           ##STR99##                                                                             C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                          O  N                                          105 CH.sub.2CHCH.sub.2                                                                           ##STR100##                                                                            OCH.sub. 3                                                                         OCH.sub.3                                                                          O  N  m.p. 219-220°                    106 CH.sub.2CH.sub.2OCH.sub.3                                                                    ##STR101##                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          107 CH.sub.2CH.sub.2OCH.sub.3                                                                    ##STR102##                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         108 CH.sub.2CH.sub.2OCH.sub.3                                                                   5-CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         109 CH.sub.2CH.sub.2OCH.sub.3                                                                   5-CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          110 CH.sub.2CH.sub.2OCH.sub.3                                                                   5-CH.sub.3                                                                             CH.sub.3                                                                           Cl  O  CH                                         111 CH.sub.2CH.sub.2OCH.sub.3                                                                   5-CH.sub.3                                                                             OCH.sub.3                                                                          Cl  O  CH                                         112 CH.sub.2CHCH.sub.2                                                                          5-CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  N  m.p. 158-162°                    113 CH.sub.2CHCH.sub.2                                                                          5-CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          114 CH.sub.2CHCH.sub.2                                                                          5-CH.sub.3                                                                             C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                          O  N                                          115 CH.sub.2CHCH.sub.2                                                                          5-CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          O  N  m.p. 160-165°                    116 CH.sub.2CHCH.sub.2                                                                          5-CH.sub.3                                                                             OCH.sub. 3                                                                         OCH.sub.3                                                                          O  CH                                         117 CH.sub.2CHCHCH.sub.3                                                                        5-CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                         118 CH.sub.2CHCHCH.sub.3                                                                        5-CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  CH m.p. 179-182°                    119 CH.sub.2CHCHCH.sub.3                                                                        5-CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          120 CH.sub.2CHCHCH.sub.3                                                                        5-NO.sub.2                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          121 CH.sub.2CHCHCH.sub.3                                                                        5-NO.sub.2                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         122 CH.sub.2CHCHCH.sub.3                                                                        5-NO.sub.2                                                                             C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                          O  N                                          123 CH.sub.2CHCHCH.sub.3                                                                        5-NO.sub.2                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          124 CH.sub.2CHCH.sub.2                                                                          5-NO.sub.2                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          125 CH.sub.2CHCH.sub.2                                                                          5-NO.sub.2                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          126 CH.sub.2CHCH.sub.2                                                                          5-NO.sub.2                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         127 CH.sub.2SCH.sub.3                                                                           5-NO.sub.2                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         128 CH.sub.2SCH.sub.3                                                                           5-NO.sub.2                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          129 CH.sub.2 SCH.sub.3                                                                          5-NO.sub.2                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          130 CH.sub.2SCH.sub.3                                                                           5-NO.sub.2                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                         131 CH.sub.2CHCH.sub.3                                                                          5-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  N  m.p. 142-143°                    132 CH.sub.2CHCH.sub.3                                                                          5-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  CH m.p. 138-139°                    133 CH.sub.2CHCH.sub.3                                                                          5-OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                         134 CH.sub.2CHCH.sub.3                                                                          5-OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          135 CH.sub.2CHCH.sub.3                                                                          5-OCH.sub.3                                                                            OCH.sub.3                                                                          C.sub.2 H.sub.5                                                                    O  N                                          136                                                                                 ##STR103##  5-OCH.sub.3                                                                            OCH.sub.3                                                                          CH.sub.3                                                                           O  N                                          137                                                                                 ##STR104##  5-OCH.sub.3                                                                            OCH.sub.3                                                                          CH.sub.3                                                                           O  CH                                         138                                                                                 ##STR105##  5-OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          139 CH.sub.2CHCHCH.sub.3                                                                        5-OCH.sub.3                                                                            OCH.sub.3                                                                          CH.sub.3                                                                           O  N                                          140 CH.sub.2CHCHCH.sub.3                                                                        5-OCH.sub. 3                                                                           OCH.sub.3                                                                          CH.sub.3                                                                           O  CH                                         141 CH.sub.2CHCHCH.sub.3                                                                        5-OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                         142 CH.sub.2CHCHCH.sub.3                                                                        5-OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          143 CH.sub.2OCH.sub.3                                                                           5-OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          144 CH.sub.2OCH.sub.3                                                                           5-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          145 CH.sub.2OCH.sub.3                                                                           5-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         146 CH.sub.2OCH.sub.3                                                                           5-OCH.sub.3                                                                            C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                          O  N                                          147 CH.sub.2CH.sub.2SCH.sub.3                                                                   5-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          148 CH.sub.2CH.sub.2SCH.sub.3                                                                   5-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         149 CH.sub.2CH.sub.2SCH.sub.3                                                                   5-OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          150 CH.sub.2CHCH.sub.2                                                                           ##STR106##                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          151 CH.sub.2CHCH.sub.2                                                                           ##STR107##                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         152                                                                                 ##STR108##                                                                                  ##STR109##                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          153                                                                                 ##STR110##                                                                                  ##STR111##                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         154                                                                                 ##STR112##  5-COOCH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         155                                                                                 ##STR113##  5-COOCH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          156 CH.sub.2CHCH.sub.2                                                                          5-COOCH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          157 CH.sub.2CHCH.sub.2                                                                          5-COOCH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         158 CH.sub.2CHCH.sub.2                                                                          5-COOCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          159 CH.sub.2CHCH.sub.2                                                                          5-COOCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                         160 CH.sub.2OC.sub.2 H.sub.5                                                                    5-COOCH.sub.3                                                                          OCH.sub.3                                                                          CH.sub.3                                                                           O  N                                          161 CH.sub.2OC.sub.2 H.sub.5                                                                    5-COOCH.sub.3                                                                          OCH.sub.3                                                                          CH.sub.3                                                                           O  N                                          162                                                                                 ##STR114##  5-CH.sub. 3                                                                            OCH.sub.3                                                                          CH.sub.3                                                                           O  N                                          163                                                                                 ##STR115##  5-CH.sub.3                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           O  CH                                         164                                                                                 ##STR116##  5-NO.sub.2                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           O  CH                                         165                                                                                 ##STR117##  5-NO.sub.2                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           O  N                                          166                                                                                 ##STR118##  5-Br    OCH.sub.3                                                                          CH.sub.3                                                                           O  N                                          167                                                                                 ##STR119##  5-Br    OCH.sub.3                                                                          CH.sub.3                                                                           O  CH                                         168                                                                                 ##STR120##  5-Cl    OCH.sub.3                                                                          CH.sub.3                                                                           O  N                                          169                                                                                 ##STR121##  5-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         170                                                                                 ##STR122##  5-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          171                                                                                 ##STR123##  5-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         172                                                                                 ##STR124##                                                                                  ##STR125##                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         173                                                                                 ##STR126##                                                                                  ##STR127##                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          174                                                                                 ##STR128##  3-CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          175                                                                                 ##STR129##  3-CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         176                                                                                 ##STR130##  6-CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          177                                                                                 ##STR131##  6-CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         178                                                                                 ##STR132##  6-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         179                                                                                 ##STR133##  6-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          180                                                                                 ##STR134##  5-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          181                                                                                 ##STR135##  5-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         182                                                                                 ##STR136##  6-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          183                                                                                 ##STR137##  6-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         184 CH.sub.2CHCH.sub.2                                                                          3-NO.sub.2                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         185 CH.sub.2CHCH.sub.2                                                                          3-NO.sub.2                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          186 CH.sub.2CHCH.sub.2                                                                          3-NO.sub.2                                                                             C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                          O  N                                          187 CH.sub.2CHCH.sub.2                                                                          3-NO.sub.2                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          188                                                                                 ##STR138##  3-NO.sub.2                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          189                                                                                 ##STR139##  3-NO.sub.2                                                                             CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         190                                                                                 ##STR140##  3-NO.sub.2                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          191                                                                                 ##STR141##  3-NO.sub. 2                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                         192                                                                                 ##STR142##  3-NO.sub.2                                                                             OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                         193                                                                                 ##STR143##  3-NO.sub.2                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           O  CH                                         194                                                                                 ##STR144##  3-NO.sub.2                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           O  N                                          195 CH.sub.2CHCH.sub.2                                                                          3-CH.sub.3                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           O  N  m.p. 255-256°                    196 CH.sub.2CHCH.sub.2                                                                          3-CH.sub.3                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           O  CH m.p. 163-164°                    197 CH.sub.2CHCH.sub.2                                                                          3-CH.sub.3                                                                             C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           O  N                                          198 CH.sub.2CHCH.sub.2                                                                          3-CH.sub.3                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           O  N  m.p. 183-184°                    199 CH.sub.2CHCH.sub.2                                                                          3-CH.sub.3                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           O  CH                                         200 CH.sub.2CHCH.sub.2                                                                          3-Cl    OCH.sub.3                                                                          CH.sub.3                                                                           O  CH                                         201 CH.sub.2CHCH.sub.2                                                                          3-Cl    OCH.sub.3                                                                          CH.sub.3                                                                           O  N                                          202 CH.sub.2CHCH.sub.2                                                                          3-Cl    OCH.sub. 3                                                                         OCH.sub.3                                                                          O  N                                          203 CH.sub.2CHCH.sub.2                                                                          3-Cl    OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                         204                                                                                 ##STR145##  3-Cl    OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          205                                                                                 ##STR146##  3-Cl    OCH.sub.3                                                                          CH.sub.3                                                                           O  N                                          206                                                                                 ##STR147##  3-Cl    OCH.sub.3                                                                          CH.sub.3                                                                           O  CH                                         207 CH.sub.2CHCHCH.sub.3                                                                        3-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          208 CH.sub.2CHCHCH.sub.3                                                                        3-Cl    CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         209                                                                                 ##STR148##  3-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         210                                                                                 ##STR149##  3-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          211 CH.sub.2CHCH.sub.2                                                                          3-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  N                                          212 CH.sub.2CHCH.sub.2                                                                          3-OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                                                          O  CH                                         213 CH.sub.2CHCH.sub.2                                                                          3-OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                          O  CH                                         214 CH.sub.2CHCH.sub.2                                                                          3-OCH.sub.3                                                                            C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                          O  N                                          215 CH.sub.2CHCH.sub.2                                                                          3-OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                          O  N                                          __________________________________________________________________________

                                      TABLE 4                                      __________________________________________________________________________      ##STR150##                                                                                                                    Physical                       No.                                                                               A                 R.sub.3 R.sub.4      X  E  data (°C.)              __________________________________________________________________________     301                                                                                ##STR151##       CH.sub.3                                                                               CH.sub.3     O  N  m.p.  95-103°           302                                                                                ##STR152##       CH.sub.3                                                                               OCH.sub.3    O  N  m.p. 142-143°           303                                                                                ##STR153##       OCH.sub.3                                                                              OCH.sub.3    O  N  m.p. 145-153°           304                                                                                ##STR154##       OCH.sub. 3                                                                             OC.sub.2 H.sub.5                                                                            O  N                                 305                                                                                ##STR155##       CH.sub.2CH.sub.3                                                                       OCH.sub.3    O  N  m.p. 150-152°           306                                                                                ##STR156##       CH.sub.2CH.sub.3                                                                       CH.sub.3     O  N  m.p. 129-130°           307                                                                                ##STR157##       Cl      OCH.sub.3    O  N                                 308                                                                                ##STR158##       OCH(CH.sub.3).sub.2                                                                    OCH.sub.3    O  N                                 309                                                                                ##STR159##       OCH(CH.sub.3).sub.2                                                                    OCH.sub.3    O  N                                 310                                                                                ##STR160##       OCH(CH.sub.3).sub.2                                                                    CH.sub.3     O  N                                 311                                                                                ##STR161##       OCH.sub.3                                                                              SCH.sub.3    O  N                                 312                                                                                ##STR162##       OC.sub.2 H.sub.5                                                                       OC.sub.2 H.sub.5                                                                            O  N  m.p. 118-120°           313                                                                                ##STR163##       OCH.sub.3                                                                              CH.sub.2 OCH.sub.3                                                                          O  N                                 314                                                                                ##STR164##       CH.sub.2 Cl                                                                            OCH.sub.3    O  N                                 315                                                                                ##STR165##       CH.sub.2 F                                                                             OCH.sub.3    O  N                                 316                                                                                ##STR166##       CH.sub.3                                                                               OCH.sub.3    O  CH m.p. 172-177°           317                                                                                ##STR167##       OCH.sub.3                                                                              OCH.sub.3    O  CH                                318                                                                                ##STR168##       CH.sub.3                                                                               CH.sub.3     O  CH                                319                                                                                ##STR169##       C.sub.2 H.sub.5                                                                        OCH.sub.3    O  CH                                320                                                                                ##STR170##       OCH.sub.3                                                                              Cl           O  CH m.p. 179-180°           321                                                                                ##STR171##       CH.sub.3                                                                               Cl           O  CH                                322                                                                                ##STR172##       CF.sub.3                                                                               OCH.sub.3    O  CH                                323                                                                                ##STR173##       CH.sub.2OCH.sub.3                                                                      OCH.sub.3    O  CH                                324                                                                                ##STR174##       Br      OCH.sub.3    O  CH                                325                                                                                ##STR175##       Br      CH.sub.3     O  CH                                326                                                                                ##STR176##       OCH.sub.3                                                                              SCH.sub.3    O  CH                                327                                                                                ##STR177##       CH.sub.3                                                                               SCH.sub.3    O  CH                                328                                                                                ##STR178##       OCH.sub.3                                                                              OC.sub.2 H.sub.5                                                                            O  CH                                329                                                                               CH.sub.2CHCHCH.sub.3                                                                             CH.sub.3                                                                               OCH.sub.3    O  N  m.p. 163-164°           330                                                                               CH.sub.2CHCHCH.sub.3                                                                             CH.sub.3                                                                               CH.sub.3     O  N                                 331                                                                               CH.sub.2CHCHCH.sub.3                                                                             C.sub.2 H.sub.5                                                                        OCH.sub.3    O  N  m.p. 139-140°           332                                                                               CH.sub.2CHCHCH.sub.3                                                                             C.sub.2 H.sub.5                                                                        CH.sub.3     O  N  m.p. 148-151°           333                                                                               CH.sub.2CHCHCH.sub.3                                                                             OCH.sub.3                                                                              OCH.sub.3    O  N  m.p. 148-149°           334                                                                               CH.sub.2CHCHCH.sub.3                                                                             OCH.sub.3                                                                              OC.sub.2 H.sub.5                                                                            O  N                                 335                                                                               CH.sub.2CHCHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                       OC.sub.2 H.sub.5                                                                            O  N                                 336                                                                               CH.sub.2CHCHCH.sub.3                                                                             CH.sub.2OCH.sub.3                                                                      OCH.sub.3    O  N                                 337                                                                               CH.sub.2CHCHCH.sub.3                                                                             CH.sub.3                                                                               OCH.sub.3    O  CH m.p. 185-186°           338                                                                               CH.sub.2CHCHCH.sub.3                                                                             OCH.sub.3                                                                              OCH.sub.3    O  CH                                339                                                                               CH.sub.2CHCHCH.sub.3                                                                             CH.sub.3                                                                               CH.sub.3     O  CH                                340                                                                               CH.sub.2CHCHCH.sub.3                                                                             CH.sub.2OCH.sub.3                                                                      OCH.sub.3    O  CH                                341                                                                               CH.sub.2CHCHCH.sub.3                                                                             CH.sub.3                                                                               Cl           O  CH                                342                                                                               CH.sub.2CHCHCH.sub.3                                                                             OCH.sub.3                                                                              Cl           O  CH                                343                                                                               CH.sub.2CHCHCG.sub.3                                                                             OCH.sub.3                                                                              OC.sub.2 H.sub.5                                                                            O  CH                                344                                                                                ##STR179##       CH.sub.3                                                                               OCH.sub.3    O  N                                 345                                                                                ##STR180##       CH.sub.3                                                                               CH.sub.3     O  N                                 346                                                                                ##STR181##       C.sub.2 H.sub.5                                                                        CH.sub.3     O  N                                 347                                                                                ##STR182##       C.sub.2 H.sub.5                                                                        OCH.sub.3    O  N                                 348                                                                                ##STR183##       OCH.sub.3                                                                              OCH.sub.3    O  N                                 349                                                                                ##STR184##       OCH.sub.3                                                                              OC.sub.2 H.sub.5                                                                            O  N                                 350                                                                                ##STR185##       OC.sub.2 H.sub.5                                                                       OC.sub.2 H.sub.5                                                                            O  N                                 351                                                                                ##STR186##       CH.sub.2OCH.sub.3                                                                      OCH.sub.3    O  N                                 352                                                                                ##STR187##       CH.sub.3                                                                               OCH.sub.3    O  CH                                353                                                                                ##STR188##       OCH.sub.3                                                                              OCH.sub.3    O  CH                                354                                                                                ##STR189##       CH.sub.3                                                                               CH.sub.3     O  CH                                355                                                                                ##STR190##       OCH.sub.3                                                                              Cl           O  CH                                356                                                                                ##STR191##       CH.sub.3                                                                               Cl           O  CH                                357                                                                                ##STR192##       OCH.sub.3                                                                              OC.sub.2 H.sub.5                                                                            O  CH                                358                                                                                ##STR193##       CH.sub.3                                                                               OCH.sub.3    O  N                                 359                                                                                ##STR194##       CH.sub.3                                                                               CH.sub.3     O  N                                 360                                                                                ##STR195##       C.sub.2 H.sub.5                                                                        CH.sub.3     O  N                                 361                                                                                ##STR196##       C.sub.2 H.sub.5                                                                        OCH.sub.3    O  N                                 362                                                                                ##STR197##       OCH.sub.3                                                                              OCH.sub.3    O  N                                 363                                                                                ##STR198##       OCH.sub.3                                                                              OC.sub.2 H.sub.5                                                                            O  N                                 364                                                                                ##STR199##       OC.sub.2 H.sub.5                                                                       OC.sub.2 H.sub.5                                                                            O  N                                 365                                                                                ##STR200##       CH.sub.2OCH.sub.3                                                                      OCH.sub.3    O  N                                 366                                                                                ##STR201##       CH.sub.3                                                                               OCH.sub.3    O  CH                                367                                                                                ##STR202##       OCH.sub.3                                                                              OCH.sub.3    O  CH                                368                                                                                ##STR203##       CH.sub.3                                                                               CH.sub.3     O  CH                                369                                                                                ##STR204##       OCH.sub.3                                                                              Cl           O  CH                                370                                                                                ##STR205##       CH.sub.3                                                                               Cl           O  CH                                371                                                                                ##STR206##       OC.sub.2 H.sub.5                                                                       OCH.sub.3    O  CH                                372                                                                                ##STR207##       CH.sub.2OCH.sub.3                                                                      OCH.sub.3    O  CH                                373                                                                               CH.sub.2OCH.sub.3 CH.sub.3                                                                               OCH.sub.3    O  N  m.p. 155-157°           374                                                                               CH.sub.2OCH.sub.3 OCH.sub.3                                                                              OCH.sub.3    O  N                                 375                                                                               CH.sub.2OCH.sub.3 C.sub.2 H.sub.5                                                                        OCH.sub.3    O  N                                 376                                                                               CH.sub.2OCH.sub.3 C.sub.2 H.sub.5                                                                        CH.sub.3     O  N                                 377                                                                               CH.sub.2OCH.sub.3 OCH.sub.3                                                                              OCH.sub.3    O  N                                 378                                                                               CH.sub.2OCH.sub.3 OCH.sub.3                                                                              OC.sub.2 H.sub.5                                                                            O  N                                 379                                                                               CH.sub.2OCH.sub.3 OC.sub.2 H.sub.5                                                                       OC.sub.2 H.sub.5                                                                            O  N                                 380                                                                               CH.sub.2OCH.sub.3 CH.sub.2OCH.sub.3                                                                      OCH.sub.3    O  N                                 381                                                                               CH.sub.2OCH.sub.3 OCH.sub.3                                                                              SCH.sub.3    O  N                                 382                                                                               CH.sub.2OCH.sub.3 OCH.sub.3                                                                              CH.sub.3     O  CH m.p. 168-175°           383                                                                               CH.sub.2OCH.sub.3 OCH.sub.3                                                                              OCH.sub.3    O  CH                                384                                                                               CH.sub.2OCH.sub.3 CH.sub.3                                                                               CH.sub.3     O  CH                                385                                                                               CH.sub.2OCH.sub.3 CH.sub.3                                                                               Cl           O  CH m.p. 137-143°           386                                                                               CH.sub.2OCH.sub. 3                                                                               OCH.sub.3                                                                              Cl           O  CH                                387                                                                               CH.sub.2OCH.sub.3 C.sub.2 H.sub.5                                                                        OCH.sub.3    O  CH                                388                                                                               CH.sub.2OCH.sub.3 OC.sub.2 H.sub.5                                                                       OCH.sub.3    O  CH                                389                                                                                ##STR208##       C.sub.2 H.sub.5                                                                        OCH.sub.3    O  CH                                390                                                                                ##STR209##       C.sub.2 H.sub.5                                                                        OCH.sub.3    O  CH                                391                                                                               CH.sub.2CHCHCH.sub.3                                                                             C.sub.2 H.sub.5                                                                        OCH.sub.3    O  CH                                392                                                                               CH.sub.2SCH.sub.3 CH.sub.3                                                                               OCH.sub.3    O  N                                 393                                                                               CH.sub.2SCH.sub.3 CH.sub.3                                                                               CH.sub.3     O  N                                 394                                                                               CH.sub.2SCH.sub.3 C.sub.2 H.sub.5                                                                        CH.sub.3     O  N                                 395                                                                               CH.sub.2SCH.sub.3 C.sub.2 H.sub.5                                                                        OCH.sub.3    O  N                                 396                                                                               CH.sub.2SCH.sub.3 OCH.sub.3                                                                              OCH.sub.3    O  N                                 397                                                                               CH.sub.2SCH.sub.3 OCH.sub.3                                                                              OC.sub.2 H.sub.5                                                                            O  N                                 398                                                                               CH.sub.2SCH.sub.3 CH.sub.2OCH.sub.3                                                                      OCH.sub.3    O  N                                 399                                                                               CH.sub.2S CH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3    O  CH                                400                                                                               CH.sub.2SCH.sub.3 OCH.sub.3                                                                              OCH.sub.3    O  CH                                401                                                                               CH.sub.2SCH.sub.3 CH.sub.3                                                                               CH.sub.3     O  CH                                402                                                                               CH.sub.2SCH.sub.3 C.sub.2 H.sub.5                                                                        OCH.sub.3    O  CH                                403                                                                               CH.sub.2SCH.sub.3 OCH.sub.3                                                                              Cl           O  CH                                404                                                                               CH.sub.2SCH.sub.3 CH.sub.3                                                                               Cl           O  CH                                405                                                                               CH.sub.2SCH.sub.3 OCH.sub.3                                                                              OC.sub.2 H.sub.5                                                                            O  CH                                406                                                                               CH.sub.2CH.sub.2OC.sub.2 H.sub.5                                                                 CH.sub.3                                                                               OCH.sub.3    O  N                                 407                                                                               CH.sub.2CH.sub.2OC.sub.2 H.sub.5                                                                 CH.sub.3                                                                               CH.sub.3     O  N                                 408                                                                               CH.sub.2CH.sub.2OC.sub.2 H.sub.5                                                                 C.sub.2 H.sub.5                                                                        CH.sub.3     O  N                                 409                                                                               CH.sub.2CH.sub.2OC.sub.2 H.sub.5                                                                 C.sub.2 H.sub.5                                                                        OCH.sub.3    O  N                                 410                                                                               CH.sub.2CH.sub.2OC.sub.2 H.sub.5                                                                 OCH.sub.3                                                                              OCH.sub.3    O  N                                 411                                                                               CH.sub.2CH.sub.2OC.sub.2 H.sub.5                                                                 CH.sub.3                                                                               OCH.sub.3    O  CH                                412                                                                               CH.sub.2CH.sub.2OC.sub.2 H.sub.5                                                                 OCH.sub.3                                                                              OCH.sub.3    O  CH                                413                                                                               CH.sub.2CH.sub.2OC.sub.2 H.sub.5                                                                 OCH.sub.3                                                                              Cl           O  CH m.p. 166-168°           414                                                                               CH.sub.2CH.sub.2OC.sub.2 H.sub.5                                                                 CH.sub.3                                                                               Cl           O  CH                                415                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.3                                                                               C.sub.2 H.sub.5                                                                             S  N                                 416                                                                               CH.sub.2CHCH.sub.2                                                                               OCH.sub.3                                                                              C.sub.2 H.sub.5                                                                             S  N                                 417                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.3                                                                               OCH.sub.3    S  CH                                418                                                                               CH.sub.2CHCH.sub.2                                                                               OCH.sub.3                                                                              OCH.sub.3    S  CH                                419                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.3                                                                               OCH.sub.3    SO N                                 420                                                                               CH.sub.2CHCH.sub.2                                                                               OCH.sub.3                                                                              OCH.sub.3    SO N                                 421                                                                               CH.sub.2CHCH.sub.2                                                                               OCH.sub.3                                                                              OC.sub.2 H.sub.5                                                                            SO N                                 422                                                                               CH.sub.2CHCH.sub.2                                                                               OCH.sub.3                                                                              OCH.sub.3    SO CH                                423                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.3                                                                               OCH.sub.3    SO CH                                424                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.3                                                                               OCH.sub.3    SO.sub.2                                                                          N                                 425                                                                               CH.sub.2CHCH.sub.2                                                                                OCH.sub.3                                                                             OCH.sub.3    SO.sub.2                                                                          N                                 426                                                                               CH.sub.2CHCH.sub.2                                                                               OCH.sub.3                                                                              OCH.sub.3    SO.sub.2                                                                          CH                                427                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.3                                                                               OCH.sub.3    SO.sub.2                                                                          CH                                428                                                                               CH.sub.2CHCHCH.sub.3                                                                             CH.sub.3                                                                               OCH.sub.3    SO.sub.2                                                                          N                                 429                                                                               CH.sub.2CHCHCH.sub.3                                                                             CH.sub.3                                                                               OCH.sub.3    SO.sub.2                                                                          CH                                430                                                                               CH.sub.2CHCHCH.sub.3                                                                             CH.sub.3                                                                               OCH.sub.3    SO CH                                431                                                                               CH.sub.2CHCHCH.sub.3                                                                             CH.sub.3                                                                               OCH.sub.3    SO N                                 432                                                                               CH.sub.2SOCH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3    O  N                                 433                                                                               CH.sub.2SOCH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3    O  CH                                434                                                                               CH.sub.2SOCH.sub.3                                                                               OCH.sub.3                                                                              OCH.sub.3    O  N                                 435                                                                               CH.sub.2SOCH.sub.3                                                                               OCH.sub.3                                                                              OCH.sub.3    O  CH                                436                                                                               CH.sub.2SO.sub.2CH.sub.3                                                                         OCH.sub.3                                                                              OCH.sub.3    O  CH                                437                                                                               CH.sub.2SO.sub.2CH.sub.3                                                                         CH.sub.3                                                                               OCH.sub.3    O  CH                                438                                                                               CH.sub.2SO.sub.2CH.sub.3                                                                         CH.sub.3                                                                               CH.sub.3     O  CH                                439                                                                               CH.sub.2SO.sub.2CH.sub. 3                                                                        CH.sub.3                                                                               OCH.sub.3    O  N                                 440                                                                               CH.sub.2SO.sub.2CH.sub.3                                                                         OCH.sub.3                                                                              OCH.sub.3    O  N                                 441                                                                               CH.sub.2CH.sub.2SOCH.sub.3                                                                       OCH.sub.3                                                                              OCH.sub.3    O  N                                 442                                                                               CH.sub.2CH.sub.2SOCH.sub.3                                                                       OCH.sub.3                                                                              CH.sub.3     O  N                                 443                                                                               CH.sub.2CH.sub.2SOCH.sub.3                                                                       OCH.sub.3                                                                              CH.sub.3     O  CH                                444                                                                               CH.sub.2CH.sub.2SO.sub.2CH.sub.3                                                                 OCH.sub.3                                                                              CH.sub.3     O  CH                                445                                                                               CH.sub.2CH.sub.2SO.sub.2CH.sub.3                                                                 OCH.sub.3                                                                              CH.sub.3     O  N                                 446                                                                               CH.sub.2CH.sub.2SO.sub.2CH.sub.3                                                                 CH.sub.3                                                                               OCH.sub.3    O  N                                 447                                                                                ##STR210##       CH.sub.3                                                                               OCH.sub.3    S  N                                 448                                                                                ##STR211##       CH.sub.3                                                                               OCH.sub.3    S  CH                                449                                                                                ##STR212##       CH.sub.3                                                                               OCH.sub.3    S  CH                                450                                                                                ##STR213##       CH.sub.3                                                                               OCH.sub.3    S  N                                 451                                                                               CH.sub. 2CHCH.sub.3                                                                              CH.sub.3                                                                               OCH.sub.3    S  N                                 452                                                                               CH.sub.2CHCH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3    S  CH                                453                                                                               CH.sub.2CH.sub.2OCH.sub.3                                                                        CH.sub.3                                                                               OCH.sub.3    S  CH                                454                                                                               CH.sub.2CH.sub.2OCH.sub.3                                                                        CH.sub.3                                                                               OCH.sub.3    S  N                                 455                                                                               (CH.sub.2).sub.2CHCH.sub.2                                                                       CH.sub.3                                                                               OCH.sub.3    O  N                                 456                                                                               (CH.sub.2).sub.2CHCH.sub.2                                                                       CH.sub.3                                                                               OCH.sub.3    O  CH                                457                                                                               (CH.sub.2).sub.2CHCH.sub.2                                                                       CH.sub.3                                                                               CH.sub.3     O  N                                 458                                                                               (CH.sub.2).sub.2CHCH.sub.2                                                                       CH.sub.3                                                                               CH.sub.3     O  CH                                459                                                                               (CH.sub.2).sub.3CHCH.sub.2                                                                       CH.sub.3                                                                               OCH.sub.3    O  N                                 460                                                                               (CH.sub.2).sub.3CHCH.sub.2                                                                       CH.sub.3                                                                               OCH.sub.3    O  CH                                461                                                                                ##STR214##       CH.sub.3                                                                               OCH.sub.3    O  N                                 462                                                                                ##STR215##       CH.sub.3                                                                               OCH.sub.3    O  CH                                463                                                                               CH.sub.2OC.sub.2 H.sub.5                                                                         CH.sub.3                                                                               OCH.sub.3    O  CH                                464                                                                               CH.sub.2OC.sub.2 H.sub.5                                                                         CH.sub.3                                                                               OCH.sub.3    O  N                                 465                                                                               CH.sub.2OC.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                        OCH.sub.3    O  N                                 466                                                                               CH.sub.2OC.sub.2 H.sub.5                                                                         CH.sub.3                                                                               CH.sub.3     O  N                                 467                                                                               CH.sub.2OC.sub.2 H.sub.5                                                                         CH.sub.3                                                                               CH.sub.3     O  CH                                468                                                                               CH.sub.2CH.sub.2OCH.sub.3                                                                        CH.sub.3                                                                               CH.sub.3     O  CH                                469                                                                               CH.sub.2CH.sub.2OCH.sub.3                                                                        CH.sub.3                                                                               CH.sub.3     O  N                                 470                                                                               CH.sub.2CH.sub.2OCH.sub.3                                                                        CH.sub.3                                                                               OCH.sub.3    O  N  m.p. 134-138°           471                                                                               CH.sub.2CH.sub.2OCH.sub.3                                                                        CH.sub.3                                                                               OCH.sub.3    O  CH m.p. 160-162°           472                                                                               CH.sub.2CH.sub.2SCH.sub.3                                                                        CH.sub.3                                                                               OCH.sub.3    O  CH                                473                                                                               CH.sub.2CH.sub.2SCH.sub.3                                                                        CH.sub.3                                                                               OCH.sub.3    O  N                                 474                                                                                ##STR216##       CH.sub.3                                                                               OCH.sub.3    O  N                                 475                                                                                ##STR217##       CH.sub.3                                                                               OCH.sub.3    O  CH                                476                                                                                ##STR218##       CH.sub.3                                                                               OCH.sub.3    O  CH                                477                                                                                ##STR219##       CH.sub.3                                                                               OCH.sub.3    O  N                                 479                                                                                ##STR220##       CH.sub.3                                                                               OCH.sub.3    O  N                                 479                                                                                ##STR221##       CH.sub.3                                                                               OCH.sub.3    O  CH                                480                                                                               CH.sub.2CH.sub.2OCH.sub.2CHCH.sub.2                                                              CH.sub.3                                                                               OCH.sub.3    O  CH                                481                                                                               CH.sub.2CH.sub.2OCH.sub.2CHCH.sub.2                                                              CH.sub.3                                                                               OCH.sub.3    O  N                                 482                                                                               CClCCl.sub.2      CH.sub.3                                                                               OCH.sub.3    O  N                                 483                                                                               CClCHCl           OCH.sub.3                                                                              OCH.sub.3    O  CH                                484                                                                               CClCCl.sub.2      OCH.sub.3                                                                              OCH.sub.3    O  N                                 485                                                                               CClCCl.sub.2      CH.sub.3                                                                               OCH.sub.3    O  CH                                486                                                                               CClCCl.sub.2      OCH.sub.3                                                                              OCH.sub.3    O  CH                                487                                                                               CClCCl.sub.2      CH.sub.3                                                                               Cl           O  CH                                488                                                                               CClCCl.sub.2      OCH.sub.3                                                                              Cl           O  N                                 489                                                                               CFCF.sub.2        OCH.sub.3                                                                              Cl           O  N                                 490                                                                               CFCF.sub.2        CH.sub.3                                                                               Cl           O  CH                                491                                                                               CHCCl.sub.2       OCH.sub.3                                                                              OCH.sub.3    O  N                                 492                                                                               CHCCl.sub.2       CH.sub.3                                                                               OCH.sub.3    O  CH                                493                                                                               CHCCl.sub.2       OCH.sub.3                                                                              OCH.sub.3    O  CH                                494                                                                               CHCCl.sub.2       C.sub.2 H.sub.5                                                                        OCH.sub.3    O  N                                 495                                                                               CFCF.sub.2        C.sub.2 H.sub.5                                                                        OCH.sub.2    O  N                                 496                                                                               CClCHCl           OCH.sub.3                                                                              OCH.sub.3    S  N                                 497                                                                               CClCHCl           CH.sub.3                                                                               OCH.sub.3    O  N  m.p. 169-172°           498                                                                               CClCHCl           C.sub.2 H.sub.5                                                                        OCH.sub.3    O  N                                 499                                                                               CClCHCl           CH.sub.3                                                                               CH.sub.3     O  N                                 500                                                                               CClCHCl           OCH.sub.3                                                                              Cl           O  CH m.p. 196-198°           501                                                                               CClCHCl           OCH.sub.3                                                                              OC.sub.2 H.sub.5                                                                            O  N                                 502                                                                               CClCHCl           OCH.sub.3                                                                              OCH.sub.3    O  CH                                503                                                                               CClCHCl           C.sub.2 H.sub.5                                                                        OCH.sub.3    O  CH                                504                                                                               CClCHCl           CH.sub.3                                                                               Cl           O  CH                                505                                                                               CClCHCl           CH.sub.3                                                                               OCH.sub.3    S  CH                                506                                                                               CClCHCl           OCH.sub.3                                                                              OCH.sub.3    S  CH                                507                                                                               CFCF.sub.2        CH.sub.3                                                                               OCH.sub.3    O  N                                 508                                                                               CFCF.sub.2        OCH.sub.3                                                                              OCH.sub.3    O  N                                 509                                                                               CFCF.sub.2        CH.sub.3                                                                               OCH.sub.3    O  CH                                510                                                                               CFCF.sub.2        OCH.sub.3                                                                              OCH.sub.3    O  CH                                511                                                                               CH.sub.2CHCH.sub.2                                                                               CH(CH.sub.3).sub.2                                                                     OCH.sub.3    O  CH                                512                                                                               CH.sub.2CHCH.sub.2                                                                               OCH.sub.3                                                                              SC.sub.2 H.sub.5                                                                            O  CH                                513                                                                               CH.sub.2CHCH.sub.2                                                                               OCH.sub.3                                                                              SC.sub.2 H.sub.5                                                                            O  N                                 514                                                                               CH.sub.2CHCH.sub.2                                                                               OCH.sub.3                                                                              SCH(CH.sub.3).sub.2                                                                         O  N                                 515                                                                               CH.sub.2CHCH.sub.2                                                                               Cl      CH.sub.3     O  N  m.p. 128-130°           516                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.3                                                                               Br           O  N                                 517                                                                               CH.sub.2CHCH.sub.2                                                                               CHF.sub.2                                                                              OCH.sub.3    O  N                                 518                                                                               CH.sub.2CHCH.sub.2                                                                               CHF.sub.2                                                                              CH.sub.3     O  N                                 519                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.2 CF.sub.3                                                                      Cl           O  N                                 520                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.2 CF.sub.3                                                                      OCH.sub.3    O  N                                 521                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.2 CF.sub.3                                                                      CH.sub.3     O  N                                 522                                                                               CH.sub.2CHCH.sub.2                                                                               OC.sub.2 H.sub.5                                                                       OC.sub.2 H.sub.5                                                                            O  N  m.p. 138-142°           523                                                                               CH.sub.2CHCH.sub.2                                                                               OC.sub.2 H.sub.5                                                                       OC.sub.2 H.sub.5                                                                            O  CH                                524                                                                               CH.sub.2CHCH.sub.2                                                                               C.sub.2 H.sub.5                                                                        OCH.sub.3    O  N  m.p. 206°               525                                                                               CH.sub.2CHCH.sub.2                                                                               C.sub.2 H.sub.5                                                                        OC.sub.2 H.sub.5                                                                            O  N                                 526                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                            O  N  m.p. 129-131°           527                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.3                                                                               CH.sub.3     O  CH m.p. 180-182°           528                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.3                                                                               OCH.sub.3    O  CH m.p.  98-100°           529                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.3                                                                               Br           O  N                                 530                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.3                                                                               H            O  N                                 531                                                                               CH.sub.2CHCH.sub.2                                                                               C.sub.2 H.sub.5                                                                        Cl           O  CH                                532                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.3                                                                               Cl           O  CH m.p. 153-154°           533                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.3                                                                               SCH.sub.3    O  CH                                534                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.3                                                                               F            O  CH                                535                                                                               CH.sub.2CH CH.sub.2                                                                              CH.sub.3                                                                               Br           O  CH                                536                                                                               CH.sub.2CHCH.sub.2                                                                               C.sub.2 H.sub.5                                                                        OC.sub.2 H.sub.5                                                                            O  CH                                537                                                                               CH.sub.2CHCH.sub.2                                                                               C.sub.2 H.sub.5                                                                        SCH.sub.3    O  CH                                538                                                                               CH.sub.2CHCH.sub.2                                                                               CF.sub.3                                                                               CH.sub.3     O  CH                                539                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.2 Cl                                                                            CH.sub.3     O  CH                                540                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.2 Cl                                                                            OCH.sub.3    O  CH                                541                                                                               CH.sub.2CHCH.sub.2                                                                               OCH.sub.3                                                                              Cl           O  CH m.p. 173-179°           542                                                                               CH.sub.2CHCH.sub.2                                                                               Cl      Cl           O  CH                                543                                                                               CH.sub.2CHCH.sub.2                                                                               OCH.sub.3                                                                              SCH.sub.3    O  CH                                544                                                                               CH.sub.2CHCH.sub.2                                                                               OCH.sub.3                                                                              OCH(CH.sub.3).sub.2                                                                         O  CH                                545                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.2 F                                                                             OCH.sub.3    O  CH                                546                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.2 F                                                                             CH.sub.3     O  CH                                547                                                                               CH.sub.2CHCH.sub.2                                                                               CF.sub.3                                                                               OCH.sub.3    O  CH                                548                                                                               CH.sub.2CHCH.sub.2                                                                               C.sub.2 H.sub.5                                                                        OCH(CH.sub.3).sub.2                                                                         O  N                                 549                                                                               CH.sub.2CH CH.sub.2                                                                              C.sub.2 H.sub.5                                                                        Cl           O  N                                 550                                                                               CH.sub.2CHCH.sub.2                                                                               C.sub.2 H.sub.5                                                                        SCH.sub.3    O  N                                 551                                                                               CH.sub.2CHCH.sub.2                                                                               C.sub.2 H.sub.5                                                                        CH.sub.3     O  N  m.p. 128-131°           552                                                                               CH.sub.2CHCH.sub.2                                                                               C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                             O  N                                 553                                                                               CH.sub.2CHCH.sub.2                                                                               OCH.sub.3                                                                              OCH(CH.sub.3).sub.2                                                                         O  N  m.p. 119-120°           554                                                                               CH.sub.2CHCH.sub.2                                                                               OCH.sub.3                                                                              OCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              O  N                                 555                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.3                                                                               CH(CH.sub.3).sub.2                                                                          O  N  m.p.  96-98°            556                                                                               CH.sub.2CHCH.sub.2                                                                               CH(CH.sub.3).sub.2                                                                     Cl           O  N                                 557                                                                               CH.sub.2CHCH.sub.2                                                                               CH(CH.sub.3).sub.2                                                                     OCH.sub.3    O  N  m.p. 124-128°           558                                                                               CH.sub.2CHCH.sub.2                                                                               CH(CH.sub.3).sub.2                                                                     OC.sub.2 H.sub.5                                                                            O  N                                 559                                                                               CH.sub.2CHCH.sub.2                                                                               CH(CH.sub.3).sub.2                                                                     SCH.sub.3    O  N                                 560                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.2 Cl                                                                            CH.sub. 3    O  N                                 561                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.2 Cl                                                                            OCH.sub.3    O  N                                 562                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.2 F                                                                             CH.sub.3     O  N                                 563                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.2 F                                                                             OCH.sub.3    O  N                                 564                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.2 F                                                                             OC.sub.2 H.sub.5                                                                            O  N                                 565                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.2OCH.sub.3                                                                      C.sub.2 H.sub.5                                                                             O  N                                 566                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.2SCH.sub.3                                                                      OCH.sub.3    O  N                                 567                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.2SCH.sub.3                                                                      CH.sub.3     O  N                                 568                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.2SCH.sub.3                                                                      SCH.sub.3    O  N                                 569                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.2SCH.sub.3                                                                      Cl           O  N                                 570                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.2SCH.sub.3                                                                      OC.sub.2 H.sub.5                                                                            O  N                                 571                                                                               CH.sub.2CHCH.sub.2                                                                               SCH.sub.3                                                                              Cl           O  N                                 572                                                                               CH.sub.2CHCH.sub.2                                                                               SCH.sub.3                                                                              OCH.sub.3    O  N                                 573                                                                               CH.sub.2CHCH.sub.2                                                                               SCH.sub.3                                                                              OC.sub.2 H.sub.5                                                                            O  N                                 574                                                                               CH.sub.2CHCH.sub.2                                                                               SCH.sub.3                                                                               ##STR222##  O  N                                 575                                                                               CH.sub.2CHCH.sub.2                                                                               OCH(CH.sub.3).sub.2                                                                    Cl           O  N                                 576                                                                               CH.sub.2CHCH.sub.2                                                                               CF.sub.3                                                                               OCH.sub.3    O  N                                 577                                                                               CH.sub.2CHCH.sub.2                                                                               CF.sub.3                                                                               CH.sub.3     O  N                                 578                                                                               CH.sub.2CHCH.sub.2                                                                               CF.sub.3                                                                               OC.sub.2 H.sub.5                                                                            O  N                                 579                                                                               CH.sub.2CHCH.sub.2                                                                               CCl.sub.3                                                                              OCH.sub.3    O  N                                 580                                                                               CH.sub.2CHCH.sub.2                                                                               CCl.sub.3                                                                              SCH.sub.3    O  N                                 581                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.3                                                                               Cl           O  N  m.p. 128-130°           582                                                                               CH.sub.2CHCH.sub.2                                                                               OCH.sub.3                                                                              Cl           O  N                                 583                                                                               CH.sub.2CHCH.sub.2                                                                               OCH.sub.3                                                                              F            O  N                                 584                                                                               CH.sub.2CHCH.sub.2                                                                               OCH.sub.3                                                                              Br           O  N                                 585                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.3                                                                               F            O  N                                 586                                                                               CH.sub.2CHCH.sub.2                                                                               OCH.sub.3                                                                              OCH.sub.3    O  CH                                587                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.3                                                                               CH.sub.3     O  N  m.p. 139.141°           588                                                                                CH.sub.2CHCH.sub.2                                                                              OCH.sub.3                                                                              OC.sub.2 H.sub.5                                                                            O  N                                 589                                                                               CH.sub.2CHCH.sub.2                                                                               OCH.sub.3                                                                              OC.sub.2 H.sub.5                                                                            O  CH                                590                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.2 OCH.sub.3                                                                     OCH.sub.3    O  CH                                591                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.2 OCH.sub.3                                                                     OCH.sub.3    O  N                                 592                                                                               CH.sub.2CHCH.sub.2                                                                               C.sub.2 H.sub.5                                                                        OCH.sub.3    O  CH                                593                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.2 OCH.sub.3                                                                     CH.sub.3     O  N                                 594                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.3                                                                               OCH.sub.3    S  N                                 595                                                                               CH.sub.2CHCH.sub.2                                                                               OCH.sub.3                                                                              OCH.sub.3    O  N  m.p. 148-149°           596                                                                               CHCHCl            CH.sub.3                                                                               OCH.sub.3    O  N                                 597                                                                               CHCHCl            CH.sub.3                                                                               OCH.sub.3    S  N                                 598                                                                               CClCHCl           CH.sub.3                                                                               OCH.sub.3    O  CH                                599                                                                               CHCCl.sub.2       CH.sub.3                                                                               OCH.sub.3    O  N                                 600                                                                               CClCHCl           OCH.sub.3                                                                              OCH.sub.3    O  N                                 601                                                                               CH.sub.2CHCH.sub.2                                                                               CH.sub.3                                                                               OCH.sub.3    O  N  m.p. 146-147°           602                                                                               CH.sub.2CHCH.sub.2                                                                               OCH.sub.3                                                                              OCH.sub.3    S  N                                 __________________________________________________________________________

                  TABLE 5                                                          ______________________________________                                          ##STR223##                                                                    No.   A                R.sub.3 R.sub.4                                                                              X    E                                    ______________________________________                                         650   CH.sub.2CHCH.sub.2                                                                              CH.sub.3                                                                               OCH.sub.3                                                                            O    N                                    651   CH.sub.2CH.sub.2OCH.sub.3                                                                       CH.sub.3                                                                               OCH.sub.3                                                                            O    N                                    652   CClCHCl          CH.sub.3                                                                               OCH.sub.3                                                                            O    N                                    653   CH.sub.2OCH.sub.3                                                                               CH.sub.3                                                                               OCH.sub.3                                                                            O    N                                    654   CH.sub.2CHCHCH.sub.3                                                                            OCH.sub.3                                                                              OCH.sub.3                                                                            O    N                                    655   CH.sub.2C(CH.sub.3)CH.sub.2                                                                     CH.sub.3                                                                               OCH.sub.3                                                                            O    CH                                   ______________________________________                                    

                                      TABLE 6                                      __________________________________________________________________________      ##STR224##                                                                                    Position of                Physical data                       No.                                                                               A            XA    R.sub.1    R.sub.2                                                                             X E  (°C.)                        __________________________________________________________________________     701                                                                               CH.sub.2CHCH.sub.2                                                                          5     2-CH.sub.3 H    O N                                      702                                                                               CH.sub.2CHCH.sub.2                                                                          5     2-CH.sub.3 H    O CH                                     703                                                                                ##STR225##  5     2-CH.sub.3 H    O CH                                     704                                                                                ##STR226##  5     2-CH.sub.3 H    O N                                      705                                                                               CH.sub.2CHCHCH.sub.3                                                                        5     2-CH.sub.3 H    O N                                      706                                                                               CH.sub.2CHCHCH.sub.3                                                                        5     2-CH.sub.3 H    O CH                                     707                                                                                ##STR227##  5     2-CH.sub.3 H    O CH                                     708                                                                                ##STR228##  5     2-CH.sub.3 H    O N                                      709                                                                               CH.sub.2CHCH.sub.2                                                                          5     2-Cl       H    O N                                      710                                                                               CH.sub.2CHCH.sub.2                                                                          5     2-Cl       H    O CH                                     711                                                                                ##STR229##  5     2-Cl       H    O CH                                     712                                                                                ##STR230##  5     2-Cl       H    O N                                      713                                                                                ##STR231##  5     2-Cl       H    O N                                      714                                                                                ##STR232##  5     2-Cl       H    O CH                                     715                                                                               CH.sub.2OCH.sub.3                                                                           5     2-Cl       H    O CH                                     716                                                                               CH.sub.2OCH.sub.3                                                                           5     2-Cl       H    O N                                      717                                                                               CH.sub.2SCH.sub.3                                                                           5     2-Cl       H    O N                                      718                                                                               CH.sub.2SCH.sub. -                                                                          5     2-Cl       H    O CH                                     719                                                                               CH.sub.2CHCHCH.sub.3                                                                        5     2-Cl       H    O CH                                     720                                                                               CH.sub.2CHCHCH.sub.3                                                                        5     2-Cl       H    O N                                      721                                                                               CH.sub.2CH.sub.2OCH.sub.3                                                                   5     2-Cl       H    O N                                      722                                                                               CH.sub.2CH.sub.2OCH.sub.3                                                                   5     2-Cl       H    O CH                                     723                                                                               CH.sub.2OC.sub.2 H.sub.5                                                                    5     2-Cl       H    O N                                      724                                                                               CH.sub.2OC.sub.2 H.sub.5                                                                    5     2-Cl       H    O CH                                     725                                                                               CH.sub.2CH.sub.2SCH.sub.3                                                                   5     2-Cl       H    O CH                                     726                                                                               CH.sub.2CH.sub.2SCH.sub.3                                                                   5     2-Cl       H    O N                                      727                                                                               CH.sub.2CHCH.sub.2                                                                          3     2-CH.sub.3 H    O N                                      728                                                                               CH.sub.2CHCH.sub.2                                                                          3     2-CH.sub.3 H    O CH                                     729                                                                                ##STR233##  3     2-CH.sub.3 H    O CH                                     730                                                                                ##STR234##  3     2-CH.sub.3 H    O N                                      731                                                                               CH.sub.2CHCH.sub.2                                                                          3     2-OCH.sub.3                                                                               H    O N                                      732                                                                               CH.sub.2CHCH.sub.2                                                                          3     2-OCH.sub.3                                                                               H    O CH                                     733                                                                                ##STR235##  3     2-OCH.sub.3                                                                               H    O CH                                     734                                                                                ##STR236##  3     2-OCH.sub.3                                                                               H    O N                                      735                                                                                ##STR237##  3     2-OCH.sub.3                                                                               H    O N                                      736                                                                                ##STR238##  3     2-OCH.sub.3                                                                               H    O CH                                     737                                                                               CH.sub.2CHCHCH.sub.3                                                                        3     2-OCH.sub.3                                                                               H    O CH                                     738                                                                               CH.sub.2CHCHCH.sub.3                                                                        3     2-OCH.sub.3                                                                               H    O N                                      739                                                                               CH.sub.2CHCH.sub.2                                                                          5     2-OCH.sub.3                                                                               H    O N                                      740                                                                               CH.sub.2CHCH.sub.2                                                                          5     2-OCH.sub.3                                                                               H    O CH                                     741                                                                                ##STR239##  5     2-OCH.sub.3                                                                               H    O CH                                     742                                                                                ##STR240##  5     2-OCH.sub.3                                                                               H    O N                                      743                                                                               CH.sub.2CHCHCH.sub.3                                                                        5     2-OCH.sub.3                                                                               H    O N                                      744                                                                               CH.sub.2CHCHCH.sub.3                                                                        5     2-OCH.sub.3                                                                               H    O CH                                     745                                                                                ##STR241##  5     2-OCH.sub.3                                                                               H    O CH                                     746                                                                                ##STR242##  5     2-OCH.sub.3                                                                               H    O N                                      747                                                                               CH.sub.2CHCH.sub.2                                                                          3     5-Br       2-OCH.sub.3                                                                         O N  m.p. 258-259°                748                                                                               CH.sub.2CHCH.sub.2                                                                          3     5-Br       2-OCH.sub.3                                                                         O CH m.p. 156-167°                749                                                                                ##STR243##  3     5-Br       2-OCH.sub.3                                                                         O CH                                     750                                                                                ##STR244##  3     5-Br       2-OCH.sub.3                                                                         O N                                      751                                                                               CH.sub.2CHCH.sub.2                                                                          3     5-COOCH.sub.3                                                                             2-OCH.sub.3                                                                         O N                                      752                                                                               CH.sub.2CHCH.sub.2                                                                          3     5-COOCH.sub.3                                                                             2-OCH.sub.3                                                                         O CH                                     753                                                                                ##STR245##  3     5-COOCH.sub.3                                                                             2-OCH.sub.3                                                                         O CH                                     754                                                                                ##STR246##  3     5-COOCH.sub.3                                                                             2-OCH.sub.3                                                                         O N                                      755                                                                               CH.sub.2CHCHCH.sub.3                                                                        3     5-COOCH.sub. 3                                                                            2-OCH.sub.3                                                                         O N                                      756                                                                               CH.sub.2CHCHCH.sub.3                                                                        3     5-COOCH.sub.3                                                                             2-OCH.sub.3                                                                         O CH                                     757                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-NO.sub.2 3-CF.sub.3                                                                          O N                                      758                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-NO.sub.2 3-CF.sub.3                                                                          O CH                                     759                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-NO.sub.2 3-Cl O CH                                     760                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-NO.sub.2 3-Cl O N                                      761                                                                                ##STR247##  2     5-NO.sub.2 3-Cl O N                                      762                                                                                ##STR248##  2     5-NO.sub.2 3-Cl O CH                                     763                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-CF.sub.3 3-NO.sub.2                                                                          O CH                                     764                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-CF.sub.3 3-NO.sub.2                                                                          O N                                      765                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-CH.sub.3 3-CH.sub.3                                                                          O N                                      766                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-CH.sub.3 3-CH.sub.3                                                                          O CH                                     767                                                                               CH.sub.2CHCHCH.sub.3                                                                        2     5-CH.sub.3 3-CH.sub.3                                                                          O CH                                     768                                                                               CH.sub.2CHCHCH.sub.3                                                                        2     5-CH.sub.3 3-CH.sub.3                                                                          O N                                      769                                                                               CH.sub.2CHCHCH.sub.3                                                                        2     5-Cl       3-NO.sub.2                                                                          O N                                      770                                                                               CH.sub.2CHCHCH.sub.3                                                                        2     5-Cl       3-NO.sub.2                                                                          O CH                                     771                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-Cl       3-NO.sub.2                                                                          O CH                                     772                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-Cl       3-NO.sub.2                                                                          O N                                      773                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-Cl       3-Cl O N                                      774                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-Cl       3-Cl O CH                                     775                                                                               CH.sub.2CH.sub.2OCH.sub.3                                                                   2     5-Cl       3-Cl O CH                                     776                                                                               CH.sub.2CH.sub.2OCH.sub.3                                                                   2     5-Cl       3-Cl O N                                      777                                                                               CH.sub.2OCH.sub.3                                                                           2     5-Cl       3-Cl O N                                      778                                                                               CH.sub.2OCH.sub.3                                                                           2     5-Cl       3-Cl O CH                                     779                                                                                ##STR249##  2     5-Cl       3-Cl O CH                                     780                                                                                ##STR250##  2     5-Cl       3-Cl O N                                      781                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-Br       3-OCH.sub.3                                                                         O N                                      782                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-Br       3-OCH.sub.3                                                                         O CH                                     783                                                                               CH.sub.2CHCH.sub.2                                                                          3     5-Br       2-OCH.sub. 3                                                                        O CH                                     784                                                                               CH.sub.2CHCH.sub.2                                                                          3     5-Br       2-OCH.sub.3                                                                         O N                                      785                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-COOCH.sub.3                                                                             3-OCH.sub.3                                                                         O N                                      786                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-COOCH.sub.3                                                                             3-OCH.sub.3                                                                         O CH                                     787                                                                               CH.sub.2CHCH.sub.2                                                                          3     5-COOCH.sub.3                                                                             2-OCH.sub.3                                                                         O CH                                     788                                                                               CH.sub.2CHCH.sub.2                                                                          3     5-COOCH.sub.3                                                                             2-OCH.sub.3                                                                         O N                                      789                                                                                ##STR251##  3     5-COOCH.sub.3                                                                             2-OCH.sub.3                                                                         O N                                      790                                                                                ##STR252##  3     5-COOCH.sub.3                                                                             2-OCH.sub.3                                                                         O CH                                     791                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-CH.sub.3 3-Br O CH                                     792                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-CH.sub.3 3-Br O N                                      793                                                                               CH.sub.2OCH.sub.3                                                                           2     5-CH.sub.3 3-Br O N                                      794                                                                               CH.sub.2OCH.sub.3                                                                           2     5-CH.sub.3 3-Br O CH                                     795                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-Br       3-NO.sub.2                                                                          O N                                      796                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-Br       3-NO.sub.2                                                                          O CH                                     797                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-Cl       3-Br O CH                                     798                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-Cl       3-Br O N  m.p. 175°                    799                                                                                ##STR253##  2     5-Cl       3-Br O N                                      800                                                                                ##STR254##  2     5-Cl       3-Br O CH                                     801                                                                               CH.sub.2CH.sub.2OCH.sub.3                                                                   2     5-Cl       3-Br O CH                                     802                                                                               CH.sub.2CH.sub.2OCH.sub.3                                                                   2     5-Cl       3-Br O N                                      803                                                                               CH.sub.2OCH.sub.3                                                                           5     2-NO.sub.2 H    O CH                                     804                                                                               CH.sub.2OCH.sub.3                                                                           3     H          H    S CH                                     805                                                                               CH.sub.2CH.sub.2OCH.sub.3                                                                   2     5-OC.sub.2 H.sub.4OCH.sub.3                                                               H    O N                                      806                                                                               CH.sub.2CHCH.sub.2                                                                          2     5-OCH.sub.2CHCH.sub.2                                                                     H    O N                                      807                                                                               CH.sub.2OCH.sub.3                                                                           2     5-OCH.sub.2OCH.sub.3                                                                      H    O N                                      808                                                                               CH.sub.2CH.sub.2OCH.sub.3                                                                   2     5-SC.sub.2 H.sub.4OCH.sub.3                                                               H    S N                                      809                                                                               CH.sub.2SCH.sub.3                                                                           2     5-SCH.sub.2SCH.sub.3                                                                      H    S N                                      810                                                                               CH.sub.2 SOCH.sub.3                                                                         2     5-SCH.sub.2SOCH.sub.3                                                                     H    S N                                      811                                                                               CH.sub.2SO.sub.2CH.sub.3                                                                    2     5-CH.sub.2SO.sub.2CH.sub.3                                                                H    S N                                      __________________________________________________________________________

FORMULATION EXAMPLES Example 4 Formulation Examples for liquid active ingredients of the formula I (throughout, percentages are by weight)

    ______________________________________                                         (a) Emulsifiable concentrates                                                                     (a)      (b)    (c)                                         ______________________________________                                         active ingredient  20%      10%    1%                                          calcium dodecylbenzenesulfonate                                                                    5%       4%    2%                                          castor oil polyethylene glycol                                                                     5%       4%    4%                                          ether (36 moles of ethylene                                                    oxide)                                                                         cyclohexanone      30%      20%    --                                          xylene mixture     40%      62%    93%                                         ______________________________________                                    

Emulsions of any required concentration can be produced from such concentrates by dilution with water.

    ______________________________________                                         (b) Solutions      (a)     (b)    (c)   (d)                                    ______________________________________                                         active ingredient  20%     10%     5%    1%                                    ethylene glycol monomethyl ether                                                                  30%     --     50%   50%                                    polyethylene glycol 400                                                                           --      70%    --    20%                                    N--methyl-2-pyrrolidone                                                                           50%     20%    44%   28%                                    epoxidised coconut oil                                                                            --      --      1%    1%                                    ______________________________________                                    

These solutions are suitable for application in the form of microdrops.

    ______________________________________                                         (c) Granulates      (a)     (b)                                                ______________________________________                                         active ingredient   5%      10%                                                kaolin              94%     --                                                 highly dispersed silicic acid                                                                      1%      --                                                 attapulgite         --      90%                                                ______________________________________                                    

The active ingredient is dissolved in methylene chloride, the solution is sprayed onto the carrier, and the solvent is subsequently evaporated off in vacuo.

    ______________________________________                                         (d) Dusts           (a)     (b)                                                ______________________________________                                         active ingredient   91.0%   1%                                                 highly dispersed silicic acid                                                                        1%    5%                                                 talcum              98.9%   --                                                 kaolin              --      94%                                                ______________________________________                                    

Dusts which are ready for use are obtained by intimately mixing the carriers with the active ingredient.

Example 5 Formulation examples for solid active ingredients of the formula I (throughout, percentages are by weight)

    ______________________________________                                         (a) Wettable powders                                                                              (a)     (b)      (c)                                        ______________________________________                                         active ingredient  20%     60%      0.5%                                       sodium lignosulfonate                                                                             5%      5%       5%                                         sodium laurylsulfate                                                                              3%      --       --                                         sodium diisobutylnaphthalene-                                                                     --      6%       6%                                         sulfonate                                                                      octylphenol polyethylene glycol                                                                   --      2%       2%                                         ether (7-8 moles of ethylene                                                   oxide)                                                                         highly dispersed silicic acid                                                                     5%      27%      27%                                        kaolin             67%     --       --                                         sodium chloride    --      --       59.5%                                      ______________________________________                                    

The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground is a suitable mill, affording wettable powders which can be diluted with water to give suspensions of the desired concentration.

    ______________________________________                                         (b) Emulsifiable concentrate                                                                         (a)    (b)                                               ______________________________________                                         active ingredient     10%    1%                                                octylphenol polyethylene glycol                                                                       3%    3%                                                ether (4-5 moles of ethylene                                                   oxide)                                                                         calcium dodecylbenzenesulfonate                                                                       3%    3%                                                castor oil polyglycol ether                                                                           4%    4%                                                (36 moles of ethylene oxide)                                                   cyclohexanone         30%    10%                                               xylene mixture        50%    79%                                               ______________________________________                                    

Emulsions of any required concentration can be obtained from this concentrate by dilution with water.

    ______________________________________                                         (c) Dusts         (a)     (b)                                                  ______________________________________                                         active ingredient  0.1%    1%                                                  talcum            99.9%   --                                                   kaolin            --      99%                                                  ______________________________________                                    

Dusts which are ready for use are obtained by mixing the active ingredient with the carriers, and grinding the mixture in a suitable mill.

    ______________________________________                                         (d) Extruder granulate                                                                             (a)    (b)                                                 ______________________________________                                         active ingredient   10%    1%                                                  sodium lignosulfonate                                                                               2%    2%                                                  carboxymethylcellulose                                                                              1%    1%                                                  kaolin              87%    96%                                                 ______________________________________                                    

The active ingredient is mixed and ground with the adjuvants, and the mixture is subsequently moistened with water. The mixture is extruded and then dried in a stream of air.

    ______________________________________                                         (e) Coated granulate                                                           ______________________________________                                         active ingredient  3%                                                          polyethylene glycol 200                                                                           3%                                                          kaolin             94%                                                         ______________________________________                                    

The finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granulates are obtained in this manner.

    ______________________________________                                         (f) Suspension concentrate                                                                           (a)     (b)                                              ______________________________________                                         active ingredient     40%     5%                                               ethylene glycol       10%     10%                                              nonylphenol polyethylene glycol                                                                       6%     1%                                               ether (15 moles of ethylene                                                    oxide)                                                                         sodium lignosulfonate 10%     5%                                               carboxymethylcellulose                                                                                1%     1%                                               37% aqueous formaldehyde solution                                                                    0.2%    0.2%                                             silicone oil in the form of a 75%                                                                    0.8%    0.8%                                             aqueous emulsion                                                               water                 32%     77%                                              ______________________________________                                    

The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired concentration can be obtained by dilution with water.

    ______________________________________                                         (g) Salt solution                                                              ______________________________________                                         active ingredient     5%                                                       isopropylamine        1%                                                       octylphenol polyethylene glycol                                                                      3%                                                       ether (78 moles of ethylene oxide)                                             water                 91%                                                      ______________________________________                                    

BIOLOGICAL EXAMPLES Example 6 Preemergence herbicidal action

In a greenhouse, plant seeds are sown in flower pots of 12-15 cm diameter. Immediately after sowing, the surface of the soil is treated with an aqueous dispersion or solution of the compounds to be tested. Concentrations of 4 kg a.i./ha are employed. The pots are then kept in the greenhouse at 22°-25° C. and 50-70% relative humidity. The test is evaluated 3 weeks later in accordance with the following rating:

1=plants totally withered

2-3=very pronounced action

4-6=medium action

7-8=insignificant action

9=no action (asuntreated controls)

    ______________________________________                                         Test Results (preemergence):                                                   Action rate of                                                                 application                                                                    kg a.i./ha     Compound 601                                                    Test plant     0.25   0.12      0.06 0.03                                      ______________________________________                                         Wheat          4      7         9    9                                         Avena fatua    2      2         3    4                                         Alopecurus myos.                                                                              2      2         2    2                                         Echinochloa c.g.                                                                              2      2         2    2                                         Rottboellia ex.                                                                               2      3         3    3                                         Cyperus escul. 3      3         3    3                                         Cotton         2      2         2    3                                         Abutilon       1      1         2    2                                         Xanthium Sp.   2      3         3    3                                         Chenopodium Sp.                                                                               1      1         2    2                                         Ipomoea        2      2         2    2                                         Sinapis        2      2         2    2                                         Galium aparine 2      2         2    3                                         Viola tricolor 2      2         2    2                                         ______________________________________                                    

Example 7 Postemergence herbicidal action (contact action)

A number of weeds and cultivated plants in pots, both monocots and dicots, are sprayed postemergence, in the 4- to 6-leaf stage, with an aqueous active ingredient dispersion at a rate of application of 4 kg a.i./ha, and then kept at 24°-26° C. and 45-60% relative humidity. The test is evaluated 15 days after treatment and the action is assessed in accordance with the same rating as in Example 6.

    ______________________________________                                         Test Results (postemergence):                                                  Action rate of                                                                 application                                                                    kg a.i./ha     Compound 601                                                    Test plant     0.25   0.12      0.06 0.03                                      ______________________________________                                         Wheat          7      9         9    9                                         Maize          3      4         7    9                                         Dry rice       4      5         8    9                                         Avena fatua    4      5         8    9                                         Alopecurus myos.                                                                              1      2         2    2                                         Echinochloa c.g.                                                                              2      2         6    6                                         Cyperus escul. 4      5         9    9                                         Cotton         4      6         7    9                                         Abutilon       2      2         2    2                                         Xanthium Sp.   1      1         1    1                                         Chenopodium Sp.                                                                               1      2         2    2                                         Ipomoea        2      3         3    4                                         Sinapis        1      1         1    1                                         Galium aparine 1      2         2    2                                         Viola tricolor 2      2         2    2                                         ______________________________________                                    

Example 8 Inhibition of sprouting in stored potatoes

A number of commercially available potatoes of the "Urgenta" variety, without sprouts, are washed and dried. The potatoes are then immersed in emulsions of the compounds to be tested in different concentrations, placed on filter paper in plastic dishes, and kept in the dark at 14°-21° C. and 50% relative humidity. Evaluation is made 34 days after application.

The percentage weight loss of the tubers and the weight of the sprouts compared with untreated controls are simultaneously determined. A number of the compounds of formula I inhibited sprouting completely in this test. At the same time, the weight loss of the potatoes was less than 10% of the weight loss of the control potatoes.

Example 9 Growth inhibition of tropical cover crops

The test plants (centrosema plumieri and centrosema pubescens) are reared until fully grown and then cut back to a height of 60 cm. The plants are sprayed 7 days later with an aqueous emulsion of the compound to be tested. The test plants are kept at 705 relative humidity and 6000 lux artificial light for 14 hours per day, at day temperatures of 27° C. and night temperatures of 21° C. The test is evaluated 4 weeks after application.

The new growth in comparison with the control is assessed and the phytotoxicity is determined. In this test, new growth of plants treated with a number of compounds of the formula I is markedly reduced (less than 20%), without damage being caused to the test plants. 

What is claimed is:
 1. A compound of the formula ##STR255##
 2. The compound according to claim 1 which is 5-fluoro-2-hydroxybenzosulfonamide. 